TOTAL SYNTHESIS OF 6-EPI-ERYTHRONOLIDE DERIVATIVES

被引:38
作者
MULZER, J [1 ]
MARESKI, PA [1 ]
BUSCHMANN, J [1 ]
LUGER, P [1 ]
机构
[1] FREE UNIV BERLIN,INST KRISTALLOG,W-1000 BERLIN 33,GERMANY
来源
SYNTHESIS-STUTTGART | 1992年 / 1-2期
关键词
D O I
10.1055/s-1992-34154
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise convergent synthesis of 6-epi-erythronolide B 3,5-acetonide and of (9R)-dihydro-6-epi-erythronolide B from (R)-2,3-O-isopropylideneglyceraldehyde is described. The key step in the synthesis involves the coupling of two aldehydes, comprising the C1-C6 and the C9-C13 portions of the target molecule, across a formal acetylide dianion (= C7-C8 (Scheme 1).
引用
收藏
页码:215 / 228
页数:14
相关论文
共 47 条
[11]   ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS [J].
HOFFMANN, RW .
CHEMICAL REVIEWS, 1989, 89 (08) :1841-1860
[12]  
KELLER E, 1988, SCHAKAL 88 PROGRAM G
[13]   DIASTEREOSELECTIVE REDUCTION OF 9-OXO-13-TETRADECANOLIDE AND 10,10-DIMETHYL-9-OXO-13-TETRADECANOLIDE [J].
KELLER, TH ;
WEILER, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :450-452
[14]   STEREO-CONTROLLED SYNTHESIS OF ERYTHRONOLIDE-A AND ERYTHRONOLIDE-B FROM 1,6-ANHYDRO-BETA-D-GLUCOPYRANOSE (LEVOGLUCOSAN) - SKELETON ASSEMBLY IN (C9-C13)+(C7-C8)+(C1-C6) SEQUENCE [J].
KOCHETKOV, NK ;
SVIRIDOV, AF ;
ERMOLENKO, MS ;
YASHUNSKY, DV ;
BORODKIN, VS .
TETRAHEDRON, 1989, 45 (16) :5109-5136
[15]  
MANCUSO AI, 1978, J ORG CHEM, V46, P248
[16]   NOVEL MACROLACTONIZATION STRATEGY FOR THE SYNTHESIS OF ERYTHROMYCIN ANTIBIOTICS [J].
MARTIN, SF ;
YAMASHITA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5478-5480
[17]   TOTAL SYNTHESIS OF 6-DEOXYERYTHRONOLIDE-B [J].
MASAMUNE, S ;
HIRAMA, M ;
MORI, S ;
ALI, SA ;
GARVEY, DS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (06) :1568-1571
[18]   MACROLIDES - RECENT PROGRESS IN CHEMISTRY AND BIOCHEMISTRY [J].
MASAMUNE, S ;
BATES, GS ;
CORCORAN, JW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (09) :585-607
[19]  
Masamune S., 1977, ANGEW CHEM, V89, P602
[20]  
Masamune S., 1982, ALDRICHIM ACTA, V15, P47