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Issue 24, 2016
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Some chemical speculation on the biosynthesis of corallidictyals A–D

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Abstract

The efficient conversion of siphonodictyal B into the spirocyclic natural products corallidictyals A–D has been achieved via oxidative and acid catalyzed cyclizations. The oxidative cyclization of siphonodictyal B occured spontaneously under aerobic oxidation conditions, which suggests that corallidictyals A and B are possibly artefacts of the isolation process. The mechanism of the oxidative cyclization of siphonodictyal B could be described as either an anionic 5-endo-trig cyclization (which is formally disfavoured by Baldwin's rules), or as an electrocyclic reaction, of an ortho-quinone intermediate.

Graphical abstract: Some chemical speculation on the biosynthesis of corallidictyals A–D

  • This article is part of the themed collection: New Talent
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Publication details

The article was received on 20 Jan 2016, accepted on 17 Feb 2016 and first published on 22 Feb 2016


Article type: Communication
DOI: 10.1039/C6OB00171H
Citation: Org. Biomol. Chem., 2016,14, 5546-5549
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    Some chemical speculation on the biosynthesis of corallidictyals A–D

    A. W. Markwell-Heys and J. H. George, Org. Biomol. Chem., 2016, 14, 5546
    DOI: 10.1039/C6OB00171H

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