Studies directed toward the synthesis of the rutamycins. Assemblage of the polypropionate region of rutamycin B

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Studies Directed Toward the SynthesisLofthe Rutamycins. Assemblage of the Polyptopkmate Regidn of Rutamycin B David A. .EvmT Fd

De~amnmt

of chanisrry, Harvard

Howard P. Ng

Univrrslry, Cm&id@,

Massachus~

02138

2230

2231

3,; Soau, T.J, I. (1) Fix the Synthesisofcytovarich~ ~tc: Evans, D. A.; Kaldor, S. W.; Jones, T. K.;Cl&y,, Am. them. SC. 1!&0,112,7001-7031. Agem wd Charrotlicropy l%i, 474. (2) &mpson, R. Q.; H&m, M. U; Higgins, C. E. A~~r~~

. Wuthicr, v. A; K&i-kcin, W. H&v. Ch&n.AC&J19QI.67; 1208-1216. C9 Amux, B.; Garcia-Alvarez, M. C; Marazaw, C.; Bhupesh,C. -D.; Pascard, C J. Chem. Sot., Ckm. (4) Commwi. l978,318-319. (5) Evans, D. A.; Rkgm, D. L.; Jones, T. K.; K&x, S. W. J. Org. C%em.t998, S&6260&68. (a) Penning, T. D.; Djuric, S. W.; Hawk, R. A.; Kalish, V. J.; Miyashiro, J. M.; Rowe& B. W.; Yu, S. S. Synth. Commim. l!@O, 20.307-3 12. It&S, ll!%t-1156, 0) Evans, D. A; En& M. I).; Le, T.; Mandcl, N.; Man&l, Cs.J. J. Am. C&m. Sac, 19e(, (8) Evans, D. A.; Ng, ft P.; Cl&J. S.; Rieger, D. L. Tetrahedron l992,48,2127-2142 ZZO,3560.3578. (9) Evans, D. k; Chaps. IL T.; Carrcim, E. M. J. Am. Chem. Six &!&IS, (10) Takai, K.; Nit+ Ic; Utinxso, K. J. Am. Ckm. Sec. 1%6,108,7408-7410. (11) Black, W. C.; Chcnb P. , unpublished nsults, Dcparmw of CItcmiatty,HarvardUniv&sity. (12) E..s, D. A.: Urpf, F; Somers, T. C.; Clark, J. S.; Bilcxkau, M. T. J. Am. Ckm. Sot. 19!JO,Z12,8215Damk, R. E.; Coppola, G. M. Tetrahedron Lat. 1990,32,2849-2852. Fohryama, T.; Lin, S.-C.; Li, L. J. Am. Chem. Sot. I9!IO, In, 70%7O!H. Evans, D. k; Black, W. C J. Am. Chqm. Sots lW2,1Z4,226&2262. Evans, D. A.; R&r D:L; Bikdcau M. T; Uqf,.F. J. Am. Chum. Sot. l991,213,1047-1049. Doaa, D. B.; Mat&, J, C J. Org. Chem. UMI3,48,4155-4156. (a) Raouh, W. bJ. Org. Chcm. 1991,56,41514157; (b) Bv&ns,D. A.;N&an, J+V.; Taber, ‘I’.R. TOP. Stwcockm. 1982.13, l-l 15. (19) Ricgcr, D. k Dart, M J.; I$#@, J. L., un@&hcdnwltr, Dqwtmau of Qtlllioory,IlaM;rd UniM (20) (a)~~~~~~~~~~ ~)~~~~~~~~~

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(Received in USA 28 December 1992; accepted 26 January 1993)