Issue 22, 2006
From the journal:

Organic & Biomolecular Chemistry

A concise, convergent total synthesis of monocerin

John H. Cassidy,a   Christopher N. Farthing,a   Stephen P. Marsden,*b   Anders Pedersen,b   Mark Slaterb  and  Geoffrey Stempc  

* Corresponding authors

a Department of Chemistry, Imperial College, London, UK

b School of Chemistry, University of Leeds, Leeds, UK
E-mail: s.p.marsden@leeds.ac.uk
Fax: +44 113 343 6565
Tel: +44 113 343 6425

c New Frontiers Science Park, GlaxoSmithKline, Third Avenue, Harlow, Essex, UK

Abstract

A concise and convergent eight-step synthesis of the antifungal metabolite monocerin 1 is reported. The key step involves an allylsilane metathesis/aldehyde condensation sequence to establish the core 2,3,5-trisubstituted tetrahydrofuran. End-game approaches based around intramolecular Heck chemistry revealed an interesting example of formal 6-endo cyclisation, the origin of which was probed using model substrates. The synthesis was ultimately completed by a strategy involving stepwise oxidative cleavage of the C3-ethenyl substituent.

Graphical abstract: A concise, convergent total synthesis of monocerin

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Article information

DOI
https://doi.org/10.1039/B612256F
Article type
Paper
Submitted
25 Aug 2006
Accepted
19 Sep 2006
First published
04 Oct 2006

Org. Biomol. Chem., 2006,4, 4118-4126

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A concise, convergent total synthesis of monocerin

J. H. Cassidy, C. N. Farthing, S. P. Marsden, A. Pedersen, M. Slater and G. Stemp, Org. Biomol. Chem., 2006, 4, 4118 DOI: 10.1039/B612256F

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