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Synfacts 2009(4): 0351-0351  
DOI: 10.1055/s-0028-1088080
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Aburatubolactam A

Contributor(s):Philip Kocienski, Arndt W. Schmidt
J. A. Henderson, A. J. Phillips*
University of Colorado, Boulder, USA
Total Synthesis of Aburatubolactam A
Angew. Chem. Int. Ed.  2008,  47:  8499-8502  
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Further Information

Publication History

Publication Date:
23 March 2009 (online)

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Key words

aburatubolactam A - macrolactams - Saegusa oxidation

Significance

Aburatubolactam A was isolated from the culture broth of a Streptomyces sp. and displays a variety of biological activities such as cytotoxicity, antimicrobial activity and inhibition of superoxide generation. This synthesis features a ring-opening/ring-closing metathesis to construct the bicyclo[3.3.0]octane subunit and a late-stage macrolactamization.

Comment

A was synthesized by an organocatalytic, enantioselective Diels-Alder cycloaddition (er = 28:1). Allylation of D occurred with complete exo selectivity but gave predominantly the unwanted trans-diastereoisomer. Deprotonation/protonation led to a 2:1 mixture in favor of the desired cis-isomer which was separated after iodolactonization.

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