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

Xiongwei Shi, Athula Attygalle, Jerrold Meinwald

Research output: Contribution to journalArticle

5 Citations (Scopus)

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

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Beetles
Alkaloids
Nuclear magnetic resonance
Derivatives
pyrrolidine
Proton Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

Cite this

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title = "Synthesis and absolute configuration of two defensive alkaloids from the Mexican bean beetle, Epilachna varivestis",
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.",
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Synthesis and absolute configuration of two defensive alkaloids from the Mexican bean beetle, Epilachna varivestis. / Shi, Xiongwei; Attygalle, Athula; Meinwald, Jerrold.

In: Tetrahedron Letters, Vol. 38, No. 37, 15.09.1997, p. 6479-6482.

Research output: Contribution to journalArticle

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T1 - Synthesis and absolute configuration of two defensive alkaloids from the Mexican bean beetle, Epilachna varivestis

AU - Shi, Xiongwei

AU - Attygalle, Athula

AU - Meinwald, Jerrold

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