Total synthesis of preswinholide A .1. Stereoselective synthesis of the C11-C23 segment

被引:21
作者
Nagasawa, K
Shimizu, I
Nakata, T
机构
[1] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN
[2] WASEDA UNIV,SCH SCI & ENGN,DEPT APPL CHEM,SHINJUKU KU,TOKYO 169,JAPAN
关键词
D O I
10.1016/0040-4039(96)01503-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The C11-C23 segment of preswinholide A was stereoselectively synthesized based on the iterative construction of 1,3-polyol chains using a series of sequential reactions which involves the Sharpless asymmetric epoxidation of allyl alcohol and Pd-catalyzed hydrogenolysis of alkenyl oxirane with HCOOH as the key reactions. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6881 / 6884
页数:4
相关论文
共 36 条
[1]   STRUCTURE OF SWINHOLIDE-A, A NEW MACROLIDE FROM THE MARINE SPONGE THEONELLA-SWINHOEI [J].
CARMELY, S ;
KASHMAN, Y .
TETRAHEDRON LETTERS, 1985, 26 (04) :511-514
[2]  
DOI M, 1991, J ORG CHEM, V56, P3629, DOI 10.1021/jo00011a033
[3]   C-13 NMR CHEMICAL-SHIFT CORRELATIONS IN 1,3-DIOL ACETONIDES - IMPLICATIONS FOR THE STEREOCHEMICAL ASSIGNMENT OF PROPIONATE-DERIVED POLYOLS [J].
EVANS, DA ;
RIEGER, DL ;
GAGE, JR .
TETRAHEDRON LETTERS, 1990, 31 (49) :7099-7100
[4]   ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
BARTROLI, J ;
SHIH, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129
[5]   AN EFFICIENT TOTAL SYNTHESIS OF (+/-)-BREFELDIN-A [J].
GREENE, AE ;
LEDRIAN, C ;
CRABBE, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) :7583-7584
[6]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976
[7]   ABSOLUTE STEREOSTRUCTURE OF SWINHOLIDE-A, A POTENT CYTOTOXIC MACROLIDE FROM THE OKINAWAN MARINE SPONGE THEONELLA-SWINHOEI [J].
KITAGAWA, I ;
KOBAYASHI, M ;
KATORI, T ;
YAMASHITA, M ;
TANAKA, J ;
DOI, M ;
ISHIDA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3710-3712
[8]   MARINE NATURAL-PRODUCTS .23. 3 NEW CYTOTOXIC DIMERIC MACROLIDES, SWINHOLIDE-B AND SWINHOLIDE-C AND ISOSWINHOLIDE-A, CONGENERS OF SWINHOLIDE-A, FROM THE OKINAWAN MARINE SPONGE THEONELLA-SWINHOEI [J].
KOBAYASHI, M ;
TANAKA, J ;
KATORI, T ;
KITAGAWA, I .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) :2960-2966
[9]   STRUCTURE OF SWINHOLIDE-A - A POTENT CYTO-TOXIC MACROLIDE FROM THE OKINAWAN MARINE SPONGE THEONELLA-SWINHOEI [J].
KOBAYASHI, M ;
TANAKA, J ;
KATORI, T ;
MATSUURA, M ;
KITAGAWA, I .
TETRAHEDRON LETTERS, 1989, 30 (22) :2963-2966
[10]  
KOBAYASHI M, 1990, CHEM PHARM BULL, V38, P2409