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Issue 48, 2016
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Enantioselective total synthesis and structural assignment of callyspongiolide

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Abstract

We have elucidated the complete absolute configuration of callyspongiolide and unambiguously assigned its stereochemistry at the C-21 center through synthesis. Four stereoisomers of callyspongiolide were synthesized in a convergent and enantioselective manner. A late-stage Sonogashira coupling forges the diene-ynic side chain. Other notable reactions are Yonemitsu's variation of Yamaguchi macrolactonization to cyclize an alkynic seco acid, highly trans-selective Julia–Kocienski olefination, CBS reduction to set the C-21 stereocenter, and methyl cuprate addition to an unsaturated pyranone to install the C-5 methyl center.

Graphical abstract: Enantioselective total synthesis and structural assignment of callyspongiolide

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Publication details

The article was received on 19 Sep 2016, accepted on 12 Oct 2016 and first published on 20 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB02051H
Citation: Org. Biomol. Chem., 2016,14, 11357-11370
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    Enantioselective total synthesis and structural assignment of callyspongiolide

    A. K. Ghosh, L. A. Kassekert and J. D. Bungard, Org. Biomol. Chem., 2016, 14, 11357
    DOI: 10.1039/C6OB02051H

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