SYNTHESES OF (+)-(S,S)-(CIS-6-METHYLTETRAHYDROPYRAN-2-YL)ACETIC ACID AND OF (-)-(R,R)-DIDESOXY-PYRENOPHORINE USING A NEW D5-REAGENT

被引:54
作者
SEEBACH, D
POHMAKOTR, M
机构
[1] Laboratorium für Organische Chemie, Eidgenössischen Technischen Hochschule Zürich, CH-8092, ETH-Zentrum
关键词
D O I
10.1002/hlca.19790620322
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Li/K‐derivative 6 is used to synthesize the title compounds (3a and 4a) in enantiomerically pure form from (−)‐(S)‐propylene epoxide. The C,C bond forming key step leading to the hydroxyketone 7 is followed by cyclization (→, 8), Beckmann cleavage (→ 9b) and hydrolysis to 3a (recently isolated from civet). Base treatment of 3a opens the ring (10) to give the hydroxyacid 1 which is cyclized to the macrolide 4a. The synthetic usefulness of the highly nucleophilic doubly reduced dienone system 6 as d5‐reagent (see synthons 2) is thus demonstirated. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim
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页码:843 / 846
页数:4
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