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A Concise Route to Racemic Anatoxin a from Cycloocta-1,5-diene

โœ Scribed by Tse-Lok Ho; Elvira Zinurova

Book ID
102253298
Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
64 KB
Volume
89
Category
Article
ISSN
0018-019X

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โœฆ Synopsis

The synthesis of racemic anatoxin a (1a) from cycloocta-1,5-diene via its 1 : 1 cycloadduct with Nchlorosulfonyl isocyanate is described. The N-unsubstituted b-lactam 2b was converted to a b-amino ester 3 which was then submitted to a Pd-catalyzed cyclization to afford the conjugated ester 4a. The N-tosyl derivative 4b was then elaborated into N-tosylanatoxin a (1b) via a Weinreb amide.

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