Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 66, Issue 4, Pages 1075-1081Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo001200w
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Funding
- NIGMS NIH HHS [GM 53830, GM 08500] Funding Source: Medline
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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.
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