Enantio selective synthesis of (-)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one and (+)-N-Boc-4-amino-2-cyclohexen-1-one: Formal total synthesis of both enantiomers of epibatidine | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

4869135

Reference Type

Journal Article

Title

Enantio selective synthesis of (-)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one and (+)-N-Boc-4-amino-2-cyclohexen-1-one: Formal total synthesis of both enantiomers of epibatidine

Author(s)

Tachihara, T; Watanabe, H; Kitahara, T

Year

2002

Is Peer Reviewed?

Yes

Journal

Heterocycles
ISSN: 0385-5414

Volume

Issue

Page Numbers

781-785

Language

English

DOI

10.3987/com-02-9459

Web of Science Id

WOS:000175994500001

Abstract

we succeeded in the stereoselective synthesis of (-)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one ((-)-2) and (+)-N-Boc-4-amino-2-cyclohexen-1-one ((+)-3), key intermediates to (-) and (+)-epibatidine from a common chiral building block ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate (4). This constitutes the formal total synthesis of both enantiomers of epibatidine, a potent analgesic.