A short stereoselective synthesis of racemic 2-epicalvine

Basem A. Moosa; Shaikh A. Ali

doi:10.1177/1934578x1000500808

A short stereoselective synthesis of racemic 2-epicalvine

Basem A. Moosa
, Shaikh A. Ali

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The cycloaddition reaction of 6-pentyl-3,4,5,6-tetrahydropyridine 1-oxide with butyl vinyl ether was used as a key step in the short stereoselective racemic synthesis of ladybird beetle alkaloid, 2-epicalvine. The cycloadduct was subjected to quaternization with 2-bromoethanol, followed by ring opening and lactonization to afford the natural product in a one-pot reaction.

Original language	English
Pages (from-to)	1191-1194
Number of pages	4
Journal	Natural Product Communications
Volume	5
Issue number	8
DOIs	https://doi.org/10.1177/1934578x1000500808
State	Published - 2010

Keywords

Epicalvine
Natural products
Nitrone cycloaddition
Piperidines
Stereoselective synthesis

ASJC Scopus subject areas

Pharmacology
Plant Science
Drug Discovery
Complementary and alternative medicine

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10.1177/1934578x1000500808

Cite this

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abstract = "The cycloaddition reaction of 6-pentyl-3,4,5,6-tetrahydropyridine 1-oxide with butyl vinyl ether was used as a key step in the short stereoselective racemic synthesis of ladybird beetle alkaloid, 2-epicalvine. The cycloadduct was subjected to quaternization with 2-bromoethanol, followed by ring opening and lactonization to afford the natural product in a one-pot reaction.",

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AU - Ali, Shaikh A.

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AB - The cycloaddition reaction of 6-pentyl-3,4,5,6-tetrahydropyridine 1-oxide with butyl vinyl ether was used as a key step in the short stereoselective racemic synthesis of ladybird beetle alkaloid, 2-epicalvine. The cycloadduct was subjected to quaternization with 2-bromoethanol, followed by ring opening and lactonization to afford the natural product in a one-pot reaction.

KW - Epicalvine

KW - Natural products

KW - Nitrone cycloaddition

KW - Piperidines

KW - Stereoselective synthesis

UR - https://www.scopus.com/pages/publications/77956686290

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DO - 10.1177/1934578x1000500808

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ER -

A short stereoselective synthesis of racemic 2-epicalvine

Abstract

Keywords

ASJC Scopus subject areas

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