Issue 21, 2003
From the journal:

Organic & Biomolecular Chemistry

A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics†

Paul G. Bulger,a   Mark G. Moloney*a  and  Paul C. Trippiera  

* Corresponding authors

a The Department of Chemistry, Dyson Perrins Laboratory, The University of Oxford, South Parks Road, Oxford, UK

Abstract

Concise and versatile routes suitable for the synthesis of three geometric isomers of an analogue of the left hand triene sub-unit of oxazolomycin are reported. A strategy based upon a key Heck reaction was unsuccessful, and this was traced to a combination of steric encumbrance and electronic deactivation of the alkene substrate. An alternative Stille coupling strategy, however, proved to be both versatile and high yielding, and is potentially applicable to the synthesis of analogues with variation both in the side-chain geometry and in the identity of the terminal aromatic or heteroaromatic residue.

Graphical abstract: A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics

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Article information

DOI
https://doi.org/10.1039/B306925G
Article type
Paper
Submitted
17 Jun 2003
Accepted
28 Jul 2003
First published
12 Aug 2003

Org. Biomol. Chem., 2003,1, 3726-3737

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A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics

P. G. Bulger, M. G. Moloney and P. C. Trippier, Org. Biomol. Chem., 2003, 1, 3726 DOI: 10.1039/B306925G

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