Volume 28, Issue 15
Natural Products
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ChemInform Abstract: Enantioselective Synthesis of the C11-C24 Segment of Macrolactin A via Organoiron Methodology.

V. PRAHLAD

V. PRAHLAD

Dep. Chem., Marquette Univ., Milwaukee, WI 53201, USA

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W. A. DONALDSON

W. A. DONALDSON

Dep. Chem., Marquette Univ., Milwaukee, WI 53201, USA

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First published: 04 August 2010

Abstract

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ChemInform Abstract

The C11-C24 segment (XVI) of the antiviral active polyene macrolide macrolactin A is synthesized in optically active form starting from iron-complexed racemic dienoate (I). The (diene)Fe(CO)3 functionality controls both the C23 stereochemistry via a chirality relay strategy and the C15 stereocenter via a highly diastereoselective nitrile oxide- olefin cycloaddition.

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