Importance of Allylic Interactions and Stereoelectronic Effects in Dictating the Steric Course of the Reaction of Iminium Ions with Nucleophiles. An Efficient Total Synthesis of (Â±)-Gephyrotoxin | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7547028

Reference Type

Journal Article

Title

Importance of Allylic Interactions and Stereoelectronic Effects in Dictating the Steric Course of the Reaction of Iminium Ions with Nucleophiles. An Efficient Total Synthesis of (Â±)-Gephyrotoxin

Author(s)

Overman, LE; Lesuisse, D; Hashimoto, M

Year

1983

Is Peer Reviewed?

Yes

Journal

Journal of the American Chemical Society
ISSN: 0002-7863
EISSN: 1520-5126

Volume

105

Issue

Page Numbers

5373-5379

Language

English

DOI

10.1021/ja00354a031

Abstract

A stereocontrolled total synthesis of (Â±)-gephyrotoxin in 15 steps and 6.5% overall yield from benzyl trans-1,3-butadiene-1-carbamate is described. A key step is reduction of octahydroquinoline 27 from the more hindered concave a face to provide decahydroquinoline 28. This unusual transformation results from the interplay of allylic (A1,2) steric interactions and stereoelectronic effects. Â© 1983, American Chemical Society. All rights reserved.

Keywords

gephyrotoxin; drug analysis; drug identification; drug structure; drug synthesis; mass spectrometry; nonhuman; nuclear magnetic resonance; stereochemistry; theoretical study; toxin synthesis