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Issue 20, 2013
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Total synthesis and revision of the absolute configuration of seimatopolide B

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Abstract

The asymmetric total synthesis of natural seimatopolide B along with its enantiomer is described starting from readily available 5-hexen-1-ol and 3-buten-1-ol. The key steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxylation, Yamaguchi esterification and ring-closing metathesis. This asymmetric total synthesis necessitates the revision of the originally assigned (3R, 6S, 9S)-configuration to (3S, 6R, 9R).

Graphical abstract: Total synthesis and revision of the absolute configuration of seimatopolide B

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Publication details

The article was received on 31 Dec 2012, accepted on 15 Mar 2013 and first published on 15 Mar 2013


Article type: Paper
DOI: 10.1039/C3OB27518C
Citation: Org. Biomol. Chem., 2013,11, 3355-3364

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    Total synthesis and revision of the absolute configuration of seimatopolide B

    C. R. Reddy, U. Dilipkumar, M. D. Reddy and N. N. Rao, Org. Biomol. Chem., 2013, 11, 3355
    DOI: 10.1039/C3OB27518C

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