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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 SumoreeahA 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.
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Publication status
- Published
Journal
TetrahedronISSN
00404020Publisher
TetrahedronExternal DOI
Issue
2Volume
56Page range
309 - 315ISBN
0040-4020Department affiliated with
- Chemistry Publications
Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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