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Total Synthesis of Brevisamide

Overview
Journal Org Lett
Publisher American Chemical Society
Specialties Biochemistry
Chemistry
Date 2009 Jul 31
PMID 19639953
Citations 2
Authors
Olugbeminiyi O Fadeyi
Craig W Lindsley
Affiliations
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Abstract

The second total synthesis of Brevisamide, a marine cyclic ether alkaloid from Karenia brevis, is reported. This streamlined synthesis proceeds in 21 steps, 14 steps longest linear sequence, in 5.2% overall yield and features a key SmI(2) reductive cyclization step to access the tetrasubstituted pyran core.

Citing Articles

A concise asymmetric total synthesis of (+)-brevisamide.

Herrmann A, Martinez S, Zakarian A Org Lett. 2011; 13(14):3636-9.

PMID: 21678904 PMC: 3365585. DOI: 10.1021/ol201283n.

A Formal Total Synthesis of (-)-Brevisamide.

Smith 3rd A, Kutsumura N, Potuzak J Tetrahedron Lett. 2011; 52(17):2117-2119.

PMID: 21572531 PMC: 3092486. DOI: 10.1016/j.tetlet.2010.11.013.

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