Enantioselective Strategy to the Spirocyclic Core of Palau'amine and Related Bisguanidine Marine Alkaloids

An enantioselective strategy to the spirocyclic core found in the oroidin-derived family of bisguanidine marine alkaloids has been devised, premised on a biosynthetic proposal. Herein, we describe the successful implementation of this strategy, which entails a Diels−Alder reaction and a chlorination...

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Bibliographic Details
Published in:Organic letters 2001-05, Vol.3 (10), p.1535-1538
Main Authors: Dilley, Anja S, Romo, Daniel
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Amines - chemical synthesis
Guanidines - chemical synthesis
Immunosuppressive Agents - chemical synthesis
Marine Biology
Spiro Compounds - chemical synthesis
Stereoisomerism
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Summary:An enantioselective strategy to the spirocyclic core found in the oroidin-derived family of bisguanidine marine alkaloids has been devised, premised on a biosynthetic proposal. Herein, we describe the successful implementation of this strategy, which entails a Diels−Alder reaction and a chlorination/ring contraction sequence that delivers the fully functionalized spirocyclic core. In this initial report, an intermolecular chlorination delivers a cyclopentane that is epimeric at C17 relative to the palau'amines and epimeric at C11 relative to the axinellamines.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015864j