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Issue 13, 2005
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The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment

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Abstract

The fully functionalised C29–C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C–C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.

Graphical abstract: The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment

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Publication details

The article was received on 22 Mar 2005, accepted on 03 May 2005 and first published on 24 May 2005


Article type: Paper
DOI: 10.1039/B504149J
Citation: Org. Biomol. Chem., 2005,3, 2420-2430
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    The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment

    I. Paterson, M. J. Coster, D. Y.-K. Chen, J. L. Aceña, J. Bach, L. E. Keown and T. Trieselmann, Org. Biomol. Chem., 2005, 3, 2420
    DOI: 10.1039/B504149J

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