Issue 9, 2005
From the journal:

Organic & Biomolecular Chemistry

Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of β-hydroxycarbonyl compounds

Christine Le Sann,a   Dulce M. Muñoz,a   Natalie Saunders,a   Thomas J. Simpson,a   David I. Smith,b   Florilène Soulas,a   Paul Wattsa  and  Christine L. Willis*a  

* Corresponding authors

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

b Department of Isotope Chemistry and Metabolite Synthesis, Sanofi-Synthelabo Research, Alnwick Research Centre, Willowburn Avenue, Alnwick, Northumberland, UK

Abstract

A versatile approach for the enantioselective synthesis of functionalised β-hydroxy N-acetylcysteamine thiol esters has been developed which allows the facile incorporation of isotopic labels. It has been shown that a remarkable reversal of selectivity occurs in the titanium mediated aldol reaction of acyloxazolidinone 7 using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted δ-lactones.

Graphical abstract: Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of β-hydroxycarbonyl compounds

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Article information

DOI
https://doi.org/10.1039/B419492F
Article type
Paper
Submitted
05 Jan 2005
Accepted
10 Feb 2005
First published
31 Mar 2005

Org. Biomol. Chem., 2005,3, 1719-1728

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Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of β-hydroxycarbonyl compounds

C. Le Sann, D. M. Muñoz, N. Saunders, T. J. Simpson, D. I. Smith, F. Soulas, P. Watts and C. L. Willis, Org. Biomol. Chem., 2005, 3, 1719 DOI: 10.1039/B419492F

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