THE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NOVEL ICHTHYOTOXIC DIACYLGLYCEROLS, UMBRACULUMIN-A AND UMBRACULUMIN-C
被引:41
作者:
DEMEDEIROS, EF
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DEMEDEIROS, EF
HERBERT, JM
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HERBERT, JM
TAYLOR, RJK
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TAYLOR, RJK
机构:
来源:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
|
1991年
/
11期
关键词:
D O I:
10.1039/p19910002725
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The total syntheses of umbraculumin A 1 and umbraculumin C 2 in homochiral form are described. Noteworthy steps involve (i) the preparation of the key Z,E-acid 10 by organolithium addition to pyrylium salts, (ii) the use of the 4-methoxyphenylmethyl protecting group for the preparation of 1,2-diacyl glycerols and its removal using trifluoroacetic acid-anisole without significant acyl migration (DDQ removal having proved inefficient) and (iii) a new procedure for the stereoselective preparation of (Z)- and (E)-3-methylthiopropenoic acid.