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Issue 15, 2000
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Structure elucidation and synthesis of (4S,5S,6Z,8E )-5-hydroxydeca-6,8-dien-4-olide [(S,S)-sapinofuranone B]—a novel γ-lactone metabolite of Acremonium strictum

Sarah Clough,a  Mairi E. Raggatt,a  Thomas J. Simpson,*a  Christine L. Willis,a  Andrew Whitingb  and  Stephen K. Wrigleyb 
Author affiliations

* Corresponding authors

a School of Chemistry, University of Bristol, Cantock’s Close, Bristol, UK

b TerraGen Discovery (UK) Ltd, 545 Ipswich Road, Slough, UK

Abstract

The structure of (4S,5S,6Z,8E )-5-hydroxydeca-6,8-dien-4-olide, a novel metabolite of Acremonium strictum, has been established by spectroscopic studies and chemical correlation with the known L-factor. The structure has been confirmed by a total synthesis in which the asymmetric centres at C-4 and C-5 were elaborated from dimethyl L-tartrate and the 6,8-diene moiety was introduced via Stille coupling of (E )-prop-1-enyltributyltin with a (Z )-vinylic iodide. The absolute configurations of sapinofuranones A and B, recently isolated metabolites of Sphaeropsis sapinae, are shown to be the corresponding (4R,5S ) and (4R,5R) diastereomers of the A. strictum metabolite.

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Publication details

The article was received on 07 Mar 2000, accepted on 02 May 2000 and first published on 30 Jun 2000


Article type: Paper
DOI: 10.1039/B001823F
Citation: J. Chem. Soc., Perkin Trans. 1, 2000,0, 2475-2481
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    Structure elucidation and synthesis of (4S,5S,6Z,8E )-5-hydroxydeca-6,8-dien-4-olide [(S,S)-sapinofuranone B]—a novel γ-lactone metabolite of Acremonium strictum

    S. Clough, M. E. Raggatt, T. J. Simpson, C. L. Willis, A. Whiting and S. K. Wrigley, J. Chem. Soc., Perkin Trans. 1, 2000, 0, 2475
    DOI: 10.1039/B001823F

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