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Synthesis of (+ / -)-Anatoxin-a and Analogues

journal contribution
posted on 2023-06-08, 07:37 authored by Philip J Parsons, Nicholas P Camp, Neil Edwards, L Ravi Sumoreeah
A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anatoxin-a and its analogues is described, which uses a ß-lactam ring opening-transannular cyclisation sequence to set up the bridged bicyclic framework of the natural product. The synthesis involves a cycloaddition of chlorosulfonyl isocyanate with cyclooctadiene followed by Boc protection of the resulting ß-lactam. Reaction of the ß- lactam with a variety of nucleophiles, followed by selenium-mediated cyclisation and oxidation gave the skeleton of anatoxin-a bearing various sidechains. The approach offers a flexible entry to useful quantities of anatoxin-a and its analogues.

History

Publication status

  • Published

Journal

Tetrahedron

ISSN

00404020

Publisher

Tetrahedron

Issue

2

Volume

56

Page range

309 - 315

ISBN

0040-4020

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

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