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Issue 7, 2015
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Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F

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Abstract

A measure of the strength of a synthetic strategy is its versatility: specifically, whether it allows structurally distinct targets to be prepared. Herein we disclose a unified approach for the total synthesis of natural products of three distinct structural types, all of which occur naturally as racemic mixtures. The point of divergence involves the terminal alkylation of a conjugated tetrayne, and culminates in a significantly shortened synthesis of endiandric acid A (8 steps), the first total synthesis of kingianic acid E (8 steps), and a second-generation synthesis of kingianins A, D, and F (11 steps). Evidence for redox catalysis in the biosynthesis of kingianic acid E is presented.

Graphical abstract: Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F

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Publication details

The article was received on 05 Mar 2015, accepted on 27 Apr 2015 and first published on 07 May 2015


Article type: Edge Article
DOI: 10.1039/C5SC00794A
Citation: Chem. Sci., 2015,6, 3886-3890
  • Open access: Creative Commons BY license
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    Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F

    S. L. Drew, A. L. Lawrence and M. S. Sherburn, Chem. Sci., 2015, 6, 3886
    DOI: 10.1039/C5SC00794A

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