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Organic letters DOI:10.1021/ol061473z

Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: synthesis of the tricyclic core of martinellic acid.

Publication TypeJournal Article
Year of Publication2006
AuthorsNg, PY, Masse, CE, Shaw, JT
JournalOrganic letters
Volume8
Issue18
Pages3999-4002
Date Published2006/08/31
ISSN1523-7060
Abstract

Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce gamma-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-pi repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.

URLhttp://dx.doi.org/10.1021/ol061473z
DOI10.1021/ol061473z
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/16928058?dopt=Abstract