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

Parsons, Philip J, Camp, Nicholas P, Edwards, Neil and Sumoreeah, L Ravi (2000) Synthesis of (+ / -)-Anatoxin-a and Analogues. Tetrahedron, 56 (2). 309 - 315. ISSN 00404020

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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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Philip Parsons
Date Deposited: 06 Feb 2012 20:44
Last Modified: 28 Mar 2012 11:04
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