Studies on stereochemistry of theonezolides A∼C1:: Determination of absolute stereochemistry of the C-4∼C-17 fragment

被引:4
作者
Sato, M [1 ]
Takeuchi, S [1 ]
Ishibashi, M [1 ]
Kobayashi, J [1 ]
机构
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
D O I
10.1016/S0040-4020(98)00190-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute stereochemistry of the C-4 similar to C-17 fragment of theonezolides A similar to C (1 similar to 3) was established as 8S, 10R, 14S, 16S on the basis of synthesis of the two diastereomers (4a and 4b) suggested from model studies and comparison of their spectral and optical data with those of natural specimen (4) obtained from ozonolysis of 1 similar to 3. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:4819 / 4826
页数:8
相关论文
共 6 条
[1]   STEREOCONTROLLED SYNTHESIS OF THE SPIRO KETAL UNIT OF AVERMECTIN-B1A AGLYCON [J].
HANESSIAN, S ;
UGOLINI, A ;
THERIEN, M .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4427-4430
[2]   THEONEZOLIDE-A - A NOVEL POLYKETIDE NATURAL PRODUCT FROM THE OKINAWAN MARINE SPONGE THEONELLA SP [J].
KOBAYASHI, J ;
KONDO, K ;
ISHIBASHI, M ;
WALCHLI, MR ;
NAKAMURA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6661-6665
[3]  
KOBAYASHI J, IN PRESS HETEROCYCLE
[4]   THE 3,4-DIHYDRO-2H-PYRAN APPROACH TO (+)-MILBEMYCIN-BETA-3 .2. AN IMPROVED SYNTHESIS OF (2R,4S,6S,8R,9S)-2-[(5R)-(2E)-3-METHYL-5-FORMYL-HEX-2-EN-1-YL]-8,9-DIMETHYL-4-(DIMETHYL-TERT-BUTYLSILYLOXY)-1,7-DIOXA-SPIRO[5.5]UNDECANE [J].
KOCIENSKI, PJ ;
STREET, SDA ;
YEATES, C ;
CAMPBELL, SF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (10) :2189-2194
[5]   ISOLATION AND STRUCTURES OF THEONEZOLIDE-B AND THEONEZOLIDE-C FROM THE OKINAWAN MARINE SPONGE THEONELLA SP [J].
KONDO, K ;
ISHIBASHI, M ;
KOBAYASHI, J .
TETRAHEDRON, 1994, 50 (28) :8355-8362
[6]   The mode of rabbit platelet shape change and aggregation induced by theonezolide-A, a novel polyketide macrolide, isolated from the Okinawan marine sponge Theonella sp [J].
Rho, MC ;
Park, YH ;
Sasaki, S ;
Ishibashi, M ;
Kondo, K ;
Kobayashi, J ;
Ohizumi, Y .
CANADIAN JOURNAL OF PHYSIOLOGY AND PHARMACOLOGY, 1996, 74 (02) :193-199