RING ENLARGEMENT BY ALKYLATED 3-HYDROXYBUTYRATES - A SYNTHESIS OF (12S, 13R)-(-)-12-METHYL-13-TETRADECANOLIDE

被引:20
作者
KRAFT, P [1 ]
TOCHTERMANN, W [1 ]
机构
[1] CHRISTIAN ALBRECHTS UNIV KIEL,INST ORGAN CHEM,D-24098 KIEL,GERMANY
关键词
FRATER ALKYLATION; MACROLIDES; RING ENLARGEMENT; ODOR AND STRUCTURE; CIRCULAR DICHROISM;
D O I
10.1016/0040-4020(95)00664-T
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
TBS-protected iodo alkohols 6 were prepared via Frater alkylation and applied in the synthesis of optically active macrolides 5 and 10. By ring enlargement of cyclodecanone (7) the superposition molecule 5 of two macrocyclic odorants was synthesized and a conformationally fixed tricyclic macrolide 11 constructed.
引用
收藏
页码:10875 / 10882
页数:8
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