Graphical abstracts

Graphical abstracts

Mild Oxidation of Cytldlne-Siallc Acid Phoaphlte Tetrahedron Letters 40 (1999) 1 Derivatives Using Dime~yldioxh-ane. Mark D. ChappeU and Randall L. Halcomb, Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309-0215 USA

r c

c,.o,.

A¢O OA¢

"

,0o

o'-

A¢O OAc

]Expeditious Route to F unit Building Block of Moenomycin A. L TetrahedronLetters 40 (1999) 5 Ramesh Kakarla*, Manuka Ghosh, Jan A. Anderson, Richard G. Dulina and Michael J. Sofia, Intercardia Research Laboratories, 8 Cedar Brook Drive, Cranbury, N J 08852 USA Synthesis of the versatile F sugar unit building block of moenomycin A, Phenyl 2-O-levulinoyl-4-C-methyl1-thio-13-D-glucopyranosiduronic acid is described starting from phenyl l-thio-13-D-galaetopyranoside. Me

O~...0~;

I C,O2H H o ~ Q

0 OAc

O

T

TOTAL SYNTHESIS OF (+)-BREYNOLIDE

L TetrahedronLetters 40 (1999) 9 Stevan D. Burke,*Jeffrey J. Letoumeau and MarkA. Matulanko Department of Chemistry,Universityof Wisconsin-Madison,Madison, W153706-1396, USA

"~,, ./

Synthesis of (+)-breynolidofrom (R)-2-cyclohexene-l-ol via the highly oxidized hydrothiophene 12 is described. HO OH 0 m-MPMO - OHO QH H I , ,s,

/

~

~

!

.o,,,.~,,.o ~ o~ (+)-breynolide

(2)

Me

;,TBDPSO.... H,,

"OMEM

©

12

Thionucleoside Disulfide Cross-Linked Duplex DNA [

Tetrahedron Letters 39 (1998) 13

Robert S. Coleman,* Jason L. McCary, and Ronefito J. Perez Department of Chemistry, The Ohio State University, 100 West 18th Avenue Columbus, Ohio 43210-1185, USA A strategy for covalent cross-linking of duplex oligonuclcotides is described, and is dna/N-~o based on a direct base-to-base disulfide bond formed by iodine oxidation of two appropriately positioned thionucleoside bases. Cross-link formation between 4-thio-2"-deoxyuddine and 6-thio-2'-deoxyinosine is demonstrated in three sequence contexts.

ix

~. \).- N, ~--N

dna

T Adamantylchlorocarbene: characterization and rearrangement [

TetrahedronLetters 40 (1999) 17

to ¢hlorohomoadamant-3-ene. Guomin Yao, Pawel Rempala, Crystal Bashore, and Robert S. Sheridan*, Department of Chemistry, University of Nevada, Reno, NV 89557

N•

. CI

~

by=, [ ~ 10 K, A r ~

1

hv b

T L Tetrahedron Letters 40 (1999) 21

MANGANESETRIACETATEMEDIATEDOXIDATION OF HANTZSCH

1/I-DIHYDROPYRIDINES TO PYRIDINES Rajender S. Varma* and Dalip Knmar,Departmentof Chemistryand Texas Research Institutefor EnvironmentalStudies (TRIES),

Sam HoustonState University,Huntsville,Texas 77341-2117, U.S.A. A general and high yield route for the oxidative conversion of 1,4-dihydropyridines to the corresponding

pyridinesis described using a relatively benign oxidant, manganese triacetate. O

0

H5C20

O OC2H5

H3C~ "N" H

"CH3

Mn (OAc)3 AeOH, rt

R

5C20

0 OC2H5

H3C" 'N"

'CH3

Tetrahedron Letters 40 (1999) 25

N u d e o p h i l i c P e r f l u o r o a l k y l a t i o n o f Nitrones.

Derek W. Nelson, * Regina A. Easley, and Beniamin N. V. Pintea Department of Chemistry, Loyola Universityof Chicago, 6525 North Sheridan Road, Chicago, 1L 60626

Additionof TMSCF3to nitroneaafforded a,-(trifluoromethyl)hydroxylamine derivatives. Atwo step sequenceof FsCzLifollowedby TMSCIyieldedrelateda,-(pentafluoroathyl)hydmxylamine cornpounds. F3C\ H , (H3C)aSiCFa R..C.N.R ~ n OSi(CH3)3 (H3C)3CO'K+

H

R..~. ~. R'

- On

1. FsC2Li == 2. CISi(CH3)3

54-89%

F3CF2C~ H , R.C.N. R OSi(CH3)3 46-73%

Tetrahedron Letters 40 (1999) 29 REACTIONS OF HALODIAZIRINES WITH POTASSIUM ETHYL XANTHATE

Xavier Crem'y Depamnentof Chemistryand Biochemistry, Universityof Notre Dame, Notre Dame, Indiana 46556 Atylhalodiazirines react with xanthate ion to give benzonitriles and 1,2,4-thiadiazoles. S"

+ EtO~C~ s

or MeOH "

Eto/C~ /

Tetrahedron Letters 40 (1999) 33

PREPARATION AND RI~CTIVITY OF SOME

FUNCTIONALIZEDHALOMETHYLZINCCARBENOIDS. Andr6 B. Chareue*, Andr~Beaucheminand Jean-FranqoisMarcoux. D~partementde Chimie, Universit~de Monied, Montr#.al,Quebec,Canada, H3C 3J7. 1. Et2Zn, hV FG-RI

2. XCH21

Ph'~'~f"DB"

= FG-RZnCH2X

~

ph,,,"p,,v,"~nBn ,,i,f v

(x=cu)

Tetrahedron Letters 40 (1999) 37 THE REACTION OF a,~ACETYLENIC KETONE$ WITH DICYCLOHEXYLBORANE: STEREOSELECTIVESYNTHESISOF FUNCTIONALiZED TRISUBSTITUTED OLEFINS G.W. Kapalka,* Su Yu, Nan-Sheng Li, Ute Lipprandt Departments of Chemistry and Radiology; The Universityof Tennessee; Knoxville,TN 37996-1600

o

Allenox~oodnates,easily generated via the 1,4-addition of dicyclohexylboraneto (x,~ acetylenic ketones, react in situ with e~cess starting ketone to afford stereodeflned, functionalized trisubstituted olefins in high yields.

R. ~

(~BH

O

MeOH

~1]~ " R'

0 °c

R'

I

Convergent Synthesis of a Polyol Chain with

{ Tetrahedron Letters 40 (1999) 41

4-Acetoxy-l,3-dioxanesUsinga

1,1 -Bis((trimethylsilyl)methyl)ethene Linchpin

Scott D. Ryelmovsky* Olga Fryszman and Uday R. Khire Department of Chemistry, UniversiW of California, Irvine, CA 92697-2025 The anti sel~tive couplings led to polyol 12, an intermediate in the synthesis of roflomycoin.

OyO

+

OyO

+

t-Bu

OyO

t-Bu

t-Bu

,,

12

OyO hBu

Efficient Synthesis of Substituted Benzenes F r o m 1,3-Dienes o r [ Tetrahedron Letters 40 (1999) 45 1,4-Cyclohexadienes With KMnO4 U n d e r Mild Conditions Christopher M. McBride, Will Chrisman, ~ E. Hsrris md Balaimn Singmmn* Departmentof ChemiaryandB ~ l r y , U~i~fity o f ~ S~ta Cruz,SantaCruz,CA95064 Tandem Diels-AIder-permanganateo~Od~.'eeIm~edure is reported fo¢file synflleAisof substituted aromatic compounds from acyclic precursors, such as dicacs and dia~opbilcs.

2h

f

v

"~:~Et

C02St

xi

~ '

O°C' 211

CO~t

I

A NOVEL D E S Y M M E T R I Z A T I O N REACTION OF AN ACETOGENIN [ Tetrahedron Letters40 (1999) 49 P R E C U R S O R : A F O R M A L SYNTHESIS OF T R I L O B A C I N AND ASIMICIN. Zheming Ruan and David R. Mootoo*, Department of Chemistry, Hunter College/CUNY, 695 Park Avenue, New York, NY 10021 USA. The iodoetherification reaction of the alkene 5 is the key reaction in the synthesis of 13 and 16, precursors of trilobacin and asimicin.

5

12

13 or 16

I Tetrahedron Letters 40 (1999) 53

A N E W R E A G E N T FOR SOLID AND SOLUTION PHASE SYNTHESIS OF P R O T E C T E D G U A N I D I N E S FROM AMINES Yaw Pui Yong, Jennifer A. Kowalski, Jason C. Thoen and Mark A. Lipton*,

Department of Chemistry, Purdue University, WestLafayette, IN 47907 A new, more reactive reagent -- 4-Nitto-l-H-pyrazole-I-[N, N'-bis(tertbutoxycarbonyl)]-carboxamidine -- for the guanylation of amines has been developed. It affords protected guanidines in high yields and short reaction times, and should find use in solid phase synthesis.

BocHN' ~ ' NBoc

Tetrahedron Letters 40 (1999) 57

Synthesis of spiro[3,2-b][l,4]oxazin-2,2'-pyrans] b a s e d u p o n m e t h y l D-arabino-2-hexulopyranosonate Jens Andersch, Dieter Sicker,* and Horst Wilde, lnstitut fOr Organische Chemie, Universit~t Leipzig, Talstr. 35, 04103 Leipzig, Germany

Br

OAc O2Me

~,~m~,~CO2Me

OAc D

c

Novel cyclic hydroxamic acids and lactams with the spiro[p~do[3,2-b][1,4]oxazin-2,2'-Wran] skeleton were synthcsiscd from methyl D-arabino-2-bexulopyranosonatesas carbohydrate mimctics related to natural benzoxazinoid aoctal glucosidcs.

Tetrahedron Letters 40 (1999) 59 DIRECT PREPARATION OF VINYL HALIDES FROM THE CORRESPONDING KETONES AND ACETYL HALIDES Khadija Moughamir, Bouchra Mezgueldi, Aziz Atmani, H~l~ne Mestdagh, Christian Rolando Ecole Normale Sup~rieure, Dtpartement de Chimie, URA 1679 du CNRS, Processus d'Activation Mol~culaire, 24 rue Lhomond, 75231 Paris cedex 05 - France

R- R, O

+ CHsCOX

.,COO.

"~ o r CHsSOaH

R' X

xii

+

CHsCOOH

R = Ar, C H s

R' = H, CHs, n-CsH13

Tetrahedron Letters 40 (1999) 63

Ruthenium Complexes Contaildng Diamine.Based Llgands as Catalysts for Insertion of Carbenes into O-It Bonds of Alcohols F. Simal, A. Demonceau, and A.F. Noels University of Liege, Sart-Tilman (B.6a), B-4000 Liege, Belgium N2CHCO2Et RO~H

]~

RO ~ C ~ C O 2 E t

(70-95%)

[Ru]:

[Ru]

TsN--'/Ru % Q N

I CONJUGATE ADDITIONS OF ALKYLCHROMIUM REAGENTS

I

Tetrahedron Letters 40 (1999) 67

MEDIATED BY CHROMIUM(III) CHLORIDE/ MANGANESE. Jacques Aug6, , Richard Gil, Sophie Kalsey, Equipe "Synth~seOrganique S61ectiveet Chimie Organom~tallique" UniversitY,de Cergy-Pontoise, 5 Mail Gay*Lussac,Neuville-sur-Oise,95031 Cergy-Pontoise, France. Benzyl and glycosylchromiumreagentsgenerated from the correspondinghalides and the couple Cr(lll)/Mn were added to activated alkenes to afford Michael adducts. CrCI3/Mn R • ~ ~ E W G RBr + ~"~ EWG Ligand R: benzyl, glycosyl EWG: CN, CO2Me. COMe

I

[ Tetrahedron Letters 40 (1999) 71

Solid-Phase Amino-Zinc-Enolate Cyclization for the Synthesis of 3-Substituted Prolines.

i

Philippe K a r o y a n , a ' b , Antonio Triolo b , R o s s a n o Nannicini b , Danilo Giannotti b, Maria A l t a m u r a b, G ~ m r d C h a s s a i n g a and Enzo Perrotta *b. a : UMR 7613, ~ Structure et Fonction de Mol#cules Bioactives ,,, Universit# Paris VI, case 182, 4 place jussieu 75252 Paris cedex 05 ~Fra~we). ." Menarini Ricerehe S.p.A. Via Sette Santi, 3 50131 Florence (Italy)

=l 1. THF, LDA, IZnBr /./I P = (R)-a-methylbenzyl / -78°C _ ~ 12 R l = Wang resin L . N . . . ~ R 1 2. ZnBr2 L.Nfl.~.OR 1 - ~.~1~OR1 - ~ P

O

P

O

p

nucleophilic substitutions

O

Tetrahedron Letters 40 (1999) 75 M E T A L A T I O N O F 3 - T R I M E T H Y L S I L Y L PROPAIRGYL C H L O R I D E : A S T E R E O S E L E C T I V E ACCESS T O tramP R O P A R G Y L I C OXIRANES. F.Chemla*, N.Bernard and J.F.Normant*, Laboratoir¢ de Chimie des Organo-El~nents, Tour 44-45, 2 e ~age, 1) LDA, ZnBr2~ R~ " Universit~ Pierre et Marie Curie, Boite 183, 4, Place Jussieu, 75252

Pads Cedex 05, France. 3-Trimethylsilyl propargyl chloride can be metalated by LDA in the presence of zinc salts. The resulting zincioallene moiety reacts with aldehydes to give stemoselective]y tranz-disubstituted propargylic chlorohydrins which can be transformed easily into trans-disubstituted propargylic oxiranas in good yields.

xiii

2) RCHO

~1

TMS d.e. = 2 0 - 100 %

] A TWO-STEP SYNTHESIS OF THE NEW 'OCTACYCLAM' AND SOME / Tetrahedron Letters 40 (1999) 79 OTHER OCTAAZACYCLOALKANES VIA REDUCTION OF TETRAAMIDE INTERMEDIATES. Raphael Tripier. Olivier Sift. Fr6d&ic Rabiet, Franck Denat and Roger Guilard* Laboratoire d'lng~nierie Mol6culaire pour la S~peratiou et les Applications des Gaz (LIMSAG), UaM.R. n° 5633 Universit~ de Bourgogne, 6, Boulevard Gabriel, 21100 - Dijon, France. The

2+2

condensation

of

f'~

tetraamimsand diethyloxalate o~j~,.oB+H2NHN~ THF yields octaazacycloalkans after

2o-"OE~ 2

~ ~

NH

o

HN

-- cNH

HN%

"-~ BH3/THF--

O~o H~gJ

tetraoxomacrocycles.

An a s y m m e t r i c total synthesis of sanjoinine G1 Tetrahedron Letters 40 (1999) 83 Taoues Lath, Jieping Zhu* Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France

NMo2 Total synthesis of sanjoinine G1 was described featuring a key intramolecular SNAr reaction.

T

AGLYCON DIRECTED PALLADIUM I3-AI~OXY

|

I.

Tetrahedron Letters 40 (1999) 87

ELIMINATION ON CARBOHYDRATE TEMPLATES. Karim Bedjeguelal, Laure Joseph, V & o n i q u e Bolitt, Denis Sinou,*Laboratoire de Synth~se Asymdtrique, associd au CNRS, CPE Lyon, Universit$ Claude Bernard Lyon 1, 43, boulevard du 11 novembre 1918, 69622 Villeurbanne C~dex, France.

/~BDMS pd/l_

Br~OK__~_~OR

.,

. ~ 'BDMS

/--Q~__~TBDMS

Br---~ ~ O R

~

TBDMS

Pd/L

Enantiopure bicyclic compounds are obtained by palladium(0)-cyclisation o f aryl 2,3-unsaturated glycosides

Re-identification ofAspergff/us n~,J_!~_ns wA Gene to Code for a

II

Tetrahedron Letters 40 ( 1999) 91

Polyketlde Synthase of Naphthopyrone Akira Watanabe, Isao Fujii, Ushio Sankawa, ~Maria E. Mayorga, ~ William E. Timberlake,~ Yutaka Ebizuka* Grail,ate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan, IFaculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Toyama, Japan, ZMillennium Pharmaceuticals Inc., Cambridge, MA 02139, USA. 3Cereon Genomics, LLC, Cambridge, MA 02139, USA

The full-length WA polyketide synthase of Aspergillus nidulans was expressed in Aspergiilus oryzae under a-amylase promoter. Its product was identified to be a novel heptaketide naphthopyrone compound YWA1 which is considered to be a true intermediateofA. nidulans spore pigment.

xiv

HO

H3 YWA1

II

Novel Polar Cycloaddition of 1,2-Thiazinylium Salt HiroshiShimizu,*TakashiHatano,TakayukiMatsuda, and Tatsunorilwamura

Tetrahedron Letters 40 (1999) 95

Gifu Pharmaceutical University, 6-1,Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Novel polar cycloaddition of dibenzo[c,e][1,2]thiazinylium tetrafluoroborate with several 1,3-butadienes afforded new sulfur- and nitrogen-containing sulfonium heterocycles in good yields.

~ . ~ b

BF4

TL

The absolute configuration of gamblerol, a toxic m a r i n e polyether f r o m the dinoflageilate, Gambierdiscus toxicus Aldo Morohashi, Masayuld Satake and Takeshi Yasumoto Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan.

Tetrahedron Letters 4O (1999) 97

OH : Me

Me

H

H

,..:~.o.4...'.~o.:~/~ H

HO

The absolute configuration of gambierol (1) was determined

H

*

:

,'y~H 0~o

HOH

- -

-

by inversion of the C6-OH group and application of the chira]

anisotropic reagent, MTPA.

OH

Tetrahedron Letters 40 (1999) 101

Ugnan Bioeyntheeis In Liverworts J~uson/e#m tmtumnalla and ~ h~ohy#a H. Tazaki*,T. Hayalg~lla,F. I~nila~, D. Taguchi,T. Talggiwa and K. Nabeta Dept. of BioresoumeSclen,~, ObihiroUniv.of Agric.and Vet. Med., Inada-cho,C~hiro 060-8556,Japan.

OOH

H O ~ C O O H

HO~,,ICO() . H

Studiesin a cell-freesystemof liverworts, Jarneson/e~a.tumn~s and Lophoco/ea /~/erophJa~lhaveshownthe formationof (±)-1 from 4.

OH

":1/ "OH

OH

OH

4

(-,-)-1

T TOTAL SYNTHESIS OF PLAGIOCHIN D, A MACROCYCLIC L Tetrahedron Letters 40 (1999) 105 BIS(BIBENZYL) FROM LIVERWORTS BY INTRAMOLECULAR STILL-KELLY REACTION Y. Fukuyama, * H. Yaso, K. Nakamuraand M. Kodama,Institute of Pharmacognosy, Facultyof Pharmaceutical Sciences, Tokushima Bunri University,Tokushima770, Japan Plagiochin D, a unique macrocyclic bis(bibenzyl) having both a biphenyl ether and a biaryl units isolated from the liverwort, has been synthesized through intramolecular formation of the biaryl unit from dibromoperrottetin A by Pd(O) catalyzed Still-Kelly reaction.

(Me3Sn)2 toluene Br

MeO

MeO ~ ~ ' ~

~ Plagtochln D

XV

"OH

-

Tetrahedron Letters 40 (1999) 109

Stereospecificity in the Lewis Acid Promoted Allylation Reaction of 3,3-Disubstituted Allyltins toward Aldehydes YutakaNishigaichiand Akio Takuwa

Department of Material Science, FaculO,of Science and Engineering, Slu'mane Universiff 1060 Nishikawatsu-cho, Matsue,Shimane 690-8504, Japan Rz RCHO

+

BF3.OEt2

~ RE

..BF3 O"

OH

Bu3Sn-~,~z H

SnBu 3

Rz

RE

RE, R z ;~H

AN EFFICIENT ACCESS TO THE OPTICALLY ACTIVE MANZAMINE TETRACYCLIC RING SYSTEM Hideharu Uchida, Atsushi Nishida, and Masako Nakagawa*

RE

stereospec/fic

I Tetrahedron Letters 40 (1999) 113

H

.H

Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

P

I

20Mo

Tetrahedron Letters 4O (1999) 117

1H-Benzotriazol-l-yl Methanesulfonate: A Regioselective NI Mesylating Reagent. Sun Young Kim''b,Nack-Do Sungb, Joong-Kwon ChoP, and Sung Soo Kim '*, "Bio-Organic Science Division, Korea Research Institute of Chemical Technology, Taejon 305-343, Korea, hDivision of Applied Biology and Chemistry, Chungnam National University, Taejon 305-764, Korea

lH-Benzotriazol-l-ylmethanesulfonatehas beenfoundto be a reagentin selectivemesylationfor differentiatingaminogroups. RI" NH2/R2-NH2 RI " NH2 / R2" OH

O .N. + CHa--S--O--N "N II O ~

~

H O \N--S--CH 11 3 II R/I O

T A Novel Palladium-Catalyzed Cyclization of [3[ Tetrahedron Iodo-15,¥-enones Toward 2,5-Disubstituted-Furans Fen-Taft Luo*, Ammugasamy Jeevanandam, and Ashok Channaveerappa Bajji Institute of ChemisUy, Academia Sinica, Nankang, Taipei, Taiwan 11529, ROC Pd cat, Et3N

in THF at rt .~ n-C5HIt"~O ~,~ R R = Me, n-CsH1!, Ph, 2-furyl, 2-thienyl.

68 - 83% isol. yields

xvi

Letters 4O (1999) 121

I

Syntheis, Structure, and Properties of Naphthalene Fully Annelated with Bicyclo[2~]octene Frameworks Akira Matsuura, Tohru Nishinaga, and Koichi Komatsu*

{

Tetrahedron Letters 40 (

1999) 123

Institute for Chemical Research, Kyoto University, Uji, Kyotoffu 611-001 I, Japan Novel naphthalene 4 surrounded by rigid o-frameworks was synthesized and its redox behavior was investigated

4+ "

42+

I [ Tetrahedron Letters 40 (1999) 127

Selectivity in the Photo-Fries Reaction of p h e n y l Phenylacetates

Included in a Nation M e m b r a n e . Chen-Ho Tung* and Xiao-He Xu Institute of Photographic Chemistry, Chinese Academy of Sciences, Be i j i ng 100101, China Photoirradiation of phenyl phenylacetates included within a Nation membrane exclusively resulted in orthohydroxyphenones, thus achieving high selectivity in the photo-Fries reaction. "

+

+

o

OH

+

°6 R

I A NOVEL METHOD FOR THE SYNTHESIS OF A C/D-RING SYNTHON [ Tetrahedron Letters 40 (1999) 131 OF VITAMIN D DERIVATIVES FROM HYODEOXYCIIOLIC ACID Ling Jie Gao, Tian Zeng Zhao, The Institute of Chemistry, Henan Academy of Sciences, Zhengzhou. 450002, P. IL China Guang Dian Hart, Institute of Materia Medica, Peking Union Medical College, Chinese Academy of Medical Sciences, Beijing, 100050, P. It. China A new C/D-ring synthon of vitamin D is readily obtained from hyodooxycholi¢acid in 7 steps and 47% overall yield.

-

1-OH

2-

3

4_

~

5-

S_

!

WALLEMINOL AND WALLEMINONE, NOVEL CARYOPHYLLENES [ Tetrahedron Letters 40 (1999) 133 FROM THE TOXlGENIC FUNGUS WALLEMIA SEBI Michael Frank, Emily Kingston, John C. Jdfery, Maurtce O. Moss, Martin Murray, Thomas J. Simpson* and Andrew Sutherland. School of Chemi~ry,Universityof Bristol, Cantock'sClose, Bristol, BS8 ITS, UK and Me ,-,~ School of BiologicalSciences,Universityof Storey, Guildford, Surrey,GU2 5XH, UK. .]._~ ~ M e ~., The s ~ ' t u ~ of walle~111) and ~lllen~one (2) novelc/#-feaed/so-caryo~yllenesfrmnthe toxigeaic

H¢'I

fungus, Wallemiasebl, havebeea establi~ed by highfield NMR midX-raycz~tallographicffmdies,

pH

tck~-~Me (1)

xvii

"

H

l

Novel Acid Catalysed 1,4-Addition-Type Ring-Opening [ Tetrahedron Letters 40 (1999) 137 Polymerisation of Cyclic Phosphorimidates Eurico J. Cabrita, Sara X. Candeias, Aria M. Ramos, Carlos A. M. Afonso* and A. Gil Santos*

|

Chemistry Department, Faculdade de Ci~ncias e Tecnologia, Universidade Nova de Lisboa, 2825 Monte de Caparica, PORTUGAL

Novel phosphorus containing oligomers were isolated in the irnide-amiderearrangement of phosphorimidates '

o, ~.-~,

"-~o-~

,.t. to6o°c"

~, r",~ °

,

IT

L~wis~

R~o'~R

o2

"

>lsooc " Rj-. o, '~

I

Tetrahedron Letters 40 (1999) 141

A NEW APPROACH TO THE SYNTHESIS OF [ NON-RACEMIC ISOINDOLIN-I-ONE DERIVATIVES StevenM. Allin, *a ChristopherJ. Northfield,b MichaelI. Page*b andAlexandraM.Z. Slawin. a

aDepanmentof Chemistry,LoughbomoghUniversity,Loughborough,Leicestershire,LEi 1 3TU,UK; bDepartmentof Chemical& BiologicalSciences,Universityof Huddersfield,Queensgate,HuddersfleldHDI 3DH,UK.

i)CLewi H2C2I acid s ~

~,hH

d.e. = 33%

e.e,

= 33%

T Tetrahedron Letters 4O (1999) 143

A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF L 3-SUBSTITUTED ISOINDOLIN-I-ONE DERIVATIVES Steven M. Ailin,TMChristopherJ. Northfield,b MichaelI. Page*b andAlexandraM.Z. Slawin.a

aDepartmentof Chemistry, Loughbomugh University, Loughborough,Leicestershire,LE11 3TU, UK;

bDepartmentof Chemical& BiologicalSciences,Universityof Huddersfield,Queensgate,HuddersfleldHD13DH,UK. ~ R .~.= N

i) TiCl4ii) Et3Si-H

~ . ¢ ~,,phOH :

~ Ph

CH2CI2

"78°C

H~ R d.c. = to 96%

R = alkyl

Tetrahedron Letters 40 (1999) 147

EPOXIDE FORMATION IN THE FRIEDEL-CRAFTS REACTION OF ADIPOYL CHLORIDE AND BROMOBENZENE.

AndrewN. Cammidge*,RichardD. Kelseyand AmyS.H.King,Schoolof ChemicalSciences,Universityof EastAnglia,Norwich NR4 7TJ. UK. ThealuminiumchlorideeatalysedFriedel-Craflsreactionbetweenadipoylchlorideandbromobenzenehas beenre-examined.At elevated t e ~ a numberof sideproductsare producedincludinga cyclopentaneepoxide. O + .~ ~_ A ~...

AICI3 Br ~

. Br

xviii

~

O O S

r (+ other products)

I

SYNTHESIS AND DIEI S - A L D E R REACTIVITY OF [ ~Tetrahedron Letters 40 (1999) 149 CI-IIRAL 2-(ALK-1-ENYL)-I,3,2-DIAZAPltOSPHOLIDINE 2-OXIDES Peter B. Wyatt*, Carolina Villalonga-Barher and Majid Mo~evalli,Departmentof Chemistry, Queen Mary and WestfieldCollege, Universityof London, Mile Ead Road, London E1 4NS, UK

H ~CH2Ph(R=Ph'Me'etc) H ICH2Ph

~ t Adducts when R=COL)Me

cat(Ph3P)4Pd H I "CH==CHR H &21::p N Et3N/PhMe/A PhCH2

Tetrahedron Letters 40 (1999) 153 Synthetic studies on sarcodictyins and eleutherobin: synthesis of hdly functionalized cydization precursors. Simona Cecearelli, Umberto Piantlli, Ccsare Gennari.* Dip. di Chimica Organica e Industriale, Universita' di Milano, Centro CNR (Sost.Org.Nat.), via Venezian 21, 20133 Milano, Italy Unprecedented synthetic transformations were demonstrated during the preparation of advanced intermediates of type 2. o1~ o1~

PG=Protectigroup ve 2a

~

~ O.~J PG=Protectgroup ive /J,~HOO~ "OMo

R'

2b

acytotmc~

lV~a ~

Tetrahedron Letters 39 (1998) 157

wifltanuvelsl0detun,from

Soleh Kcsdaa, Slm-Geng(2aob,~Tmo-FhmWub,J ~ S w e e - t k ~ Goi~, ard K e ~ Y e o w S h ~

b~nnn~of ~

R'

~

J. V ' ~ b , Tony Sdoia, Madimloa, o

[

I

1 Tetrahedron Letters 40 (1999) 161

A NOVEL ROUTE TO (+)-ASPIDOSPERMIDINE:FIRST APPLICATIONOF "RADICAI.-POI.AR CROSSOVER" REACTIONSTO TOTAL SYNTHESIS Owen Callaghan, Christopher Lampard, Alan R. Kennedyand John A. Murphy* Department of Pure and Applied Chemistry, Universityof Strathclyde. 295 Cathedral Street, Glasgow Gl IXL, U.K. _NHCOCF~

~iA's-pid°sl - ~ern~itline]

F~COCHN~ OH

I~S~S IVIs

-N2

~ MH

xix

o

o o

X,~tRUg,, S~gapor, 11926O

The isolation of an unprecedented spiroxalactone, lateriflorone (1), and its structural elucidation__by NM_R spectral data and X-ray an~y__sisare described.

B-F4 +

i

Tetrahedron Letters 40 (1999) 165

M i c r o w a v e Irradiation : Wlttig Olefination of Lactones and Amides

G o w r a v a r a m Sabitha,* M M u r a l i d h a r Reddy, D. S r i n i v a s a n d J.S. Yadav

Indian Institute of Chemical Technology, Hyderabad 500 007, India. +

Ph3P=::CI'I--COOEr

90 sec.

~

3

1

H

COOEt

Tetrahedron Letters 40 (1999) 167 Reversal of Stereoselectivity of M g ( l l ) Catalysed 1,3-Dipolar Cycloaddition. Acceleration of Cycloaddition by M i c r o w a v e Irradiation. P e t e r M i 6 6 c h =, E u b o r F i [ e r a =*, M i c h a t K. C y r a h s k i b, T a d e u s z M. K I T g o w s k i b

°Department of Organic Chemistry, Slovak University of Technology, 812 37 Bratislava, Slovak Republic bDepartment of Chemistry, University of Warsaw, 02 093 Warsaw, Poland CO2CH3

~Mst-CNO R~ N OH -kMst Toluene

,~ R OH

CO2CH3

MSI-CNO "CO2CH3 .. CH2Cl; R..,~ /'~Mst

MeMgBr,

INFLUENCE OF REMOTE INTRAMOLECULAR HYDROGEN BONDS ON THE THERMODYNAMICS OF MOLECULAR RECOGNITION OF CIS-1,3,5-CYCLOHEXANETRICARBOXYLIC ACID. Pablo Ballester, Antoni Costa, Pere M. Dey~, Manuel Vega, Jeroni Morey, Departament de Quimica, Universitat de les Illes Balears, Palma de Mallorca, Spain, and Ghislain Deslongchamps, Department of Chemistry, University of New Brunswick, Fredericton, N.B., Canada

~)HO.,N

Tetrahedron Letters 40 (1999) 171

OH

Variable temperature binding studies and isotermal titration microcalorimetry were used to probe the thermodynamics of molecular recognition of cis-l,3,5-cyclohexanetricarboxylic acid by tripodal hosts. Remote intramolecular hydrogen bonds, used to conformationally restrict one of the hosts, exhibit a strong influence on the thermodynamic functions AH and AS, with little effect on AG.

R = H, OH ~

R

,,

-

Tetrahedron Letters 40 (1999) 175

Tandem reorganisation of 1,3-dipolar cyeloadducts of C-(4-Oxo-4H[l]benzopyran-3-yl)-N-phenylnitrone and allenic esters, leading to novel functionalized benzo[b]indolizines M.P.S. lshar* and Kamal Kumar Department o f Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar-143 005, Punjab, India.

H +

z~

~ k~Cn¢ refilLS

H.O/~_/' n - H . M e , EL

(aS. 60o/.)

xx

REDUCTIONI

STEREOSELECTIVE SULFOXIDE DIRECTED OF 1,2-DIKETO-DERIVATIVES TO ENANTIOMERICALLY PURE SYN AND ANTI 1,2-DIOLS. CORRECTION OF THE RELATIVE CONFIGURATION BY X-RAY AND CHEMICAL CORRELATION TO GONIOBUTENOLIDES A AND B. Guy Solladi~*, Gilles Hanquet, Catherine Roiland

Tetrahedron Letters 40 (1999) 177

Laboratoire de St~rC,ochimle asso¢i~ au CNRS, ECPM, Unlverslt~ Louis Pasteur 1 rue Blaise Pascal, 67008-Strasbourg, France

I- - °

oII

Meo/N..~J~N..OMe__

g

1 step.

oII

M e o I N ~"

l

S ~p ,,,,,mh

o

R'

4 Steps

-Tol

OTBS O II ~ ..S',,.Ih L v ~NI,p.Tol Syn or Anti

1 A Highly Flexible Route to Tricyelol4.3.1.0a'~] -, and Tricy¢lo[4.3.0.0~tO]decanes: A short synthesis of pupukean-2-one

I I

Tetrahedron Letters 4O (1999) 181

P. John Biju and G.S.R. Subba Rao* Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India A novel one-pot acid-catalyzed rearrangement followed by an ene reaction has been developed for the construction of tricyclo[4.3.1.03'7]decane (isotwistane) and tricyclo[4.3.0.04'l°]decanes. o

=

o

I TetrahedronLetters 40 (1999) 185 TI~ SILA-PtNMERI~ REARRANI~I~I" OF 3 , 3 - D ~ - S I L M r l I I A ! ~ S-OX]flDE S.V.Kirpichenko,EN. Susleva, A.I. AIbanov,B.A. Shainyan lrkutsk Institute of Chemistry, I Favorskii Str., Irkutsk, Russia. e-mail:[email protected]

The first exampleofthemal sila-Pummererrearrangementof cyclicorganosiliconsulfofides leading to ring expansion is found and its kinetics and activationparametersare measured. Me2SiOs=o

A ~

Me2Siko~S

xxi