Issue 5, 2009
From the journal:

Organic & Biomolecular Chemistry

Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation†

Riaz A. Bhunnoo,a   Heather Hobbs,b   Dramane I. Lainé,c   Mark E. Lighta  and  Richard C. D. Brown*a  

* Corresponding authors

a The School of Chemistry, University of Southampton, Highfield, Southampton, UK
E-mail: rcb1@soton.ac.uk
Fax: + 44 (0)2380 593781
Tel: + 44 (0)2380 594108

b GlaxoSmithKline, Gunnels Wood Road, Stevenage, UK

c GlaxoSmithKline, RI CEDD, 709 Swedeland Road, King of Prussia, PA, USA

Abstract

A short synthesis of the non-adjacent bis-THF core of the Annonaceousacetogenincis-sylvaticin (1) is described. C2 Symmetrical (Z,E,E,Z)- and (E,E,E,E)-tetraenes 5 and 6 were synthesised in six and three steps respectively from (1E,5E,9E)-cyclododeca-1,5,9-triene. Subsequent permanganate promoted asymmetric bi-directional oxidative cyclisation of tetraene 5 was used to create the non-adjacent bis-THF core of 1, installing seven of the nine stereogenic centres present in the natural product in a single step. Desymmetrisation of the oxidative cyclisation product by mono-tosylation gave access to a C11–C32 fragment of cis-sylvaticin.

Graphical abstract: Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation

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Article information

DOI
https://doi.org/10.1039/B813201A
Article type
Paper
Submitted
31 Jul 2008
Accepted
28 Nov 2008
First published
28 Jan 2009

Org. Biomol. Chem., 2009,7, 1017-1024

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Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation

R. A. Bhunnoo, H. Hobbs, D. I. Lainé, M. E. Light and R. C. D. Brown, Org. Biomol. Chem., 2009, 7, 1017 DOI: 10.1039/B813201A

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