Synthesis of unsaturated polyazamacrolides from the ladybird beetle Subcoccinella vigintiquatuorpunctata

被引：18

作者：

Gronquist, MR ^{[1
]}

Meinwald, J ^{[1
]}

机构：

[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 04期

关键词：

D O I：

10.1021/jo001200w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.

引用

页码：1075 / 1081

页数：7

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