Synthesis and absolute configuration of two defensive alkaloids from the Mexican bean beetle, Epilachna varivestis

Xiongwei Shi, Athula B. Attygalle, Jerrold Meinwald

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Abstract

Syntheses of (2S,12'R)-2-(12'-aminotridecyl)-pyrrolidine (1) and (28,12'R)-1-(2'-hydroxyethyl)-2-(12'-aminotridecyl)-pyrrolidine (2), two defensive alkaloids recently isolated from the Mexican bean beetle, Epilachna varivestis, are described. By a comparison of 1H NMR data of MTPA derivatives of natural alkaloid 2 with those of the synthetic standard, we confirm the (2S,12'R) configuration previously suggested for this alkaloid. Further support of these assignments was provided by the synthesis and 1H NMR investigation of(2S,12'S)-1, (2S,12'S)-2, and their MTPA derivatives.

Original languageEnglish
Pages (from-to)6479-6482
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number37
DOIs
StatePublished - 15 Sep 1997

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