Assembly intermediates in polyketide biosynthesis; enantioselective syntheses of beta-hydroxycarbonyl compounds

Christine Le Sann; C.L. Willis; T.J. Simpson; P. Watts; D.M. Munoz; N. Saunders; D.I. Smith; F. Soulas

doi:10.1039/b419492f

Assembly intermediates in polyketide biosynthesis; enantioselective syntheses of beta-hydroxycarbonyl compounds

Christine Le Sann, C.L. Willis, T.J. Simpson, P. Watts, D.M. Munoz, N. Saunders, D.I. Smith, F. Soulas

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

A versatile approach for the enantioselective synthesis of functionalised beta-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 the acyloxazolidone intermediate using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted gamma-lactones.

Original language	English
Pages (from-to)	1719-1728
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	3 (9)
Issue number	9
DOIs	https://doi.org/10.1039/b419492f
Publication status	Published - 07 Jan 2005

ASJC Scopus subject areas

General Biochemistry,Genetics and Molecular Biology
General Chemistry

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abstract = "A versatile approach for the enantioselective synthesis of functionalised beta-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 the acyloxazolidone intermediate using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted gamma-lactones.",

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AU - Le Sann, Christine

AU - Willis, C.L.

AU - Simpson, T.J.

AU - Watts, P.

AU - Munoz, D.M.

AU - Saunders, N.

AU - Smith, D.I.

AU - Soulas, F.

PY - 2005/1/7

Y1 - 2005/1/7

N2 - A versatile approach for the enantioselective synthesis of functionalised beta-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 the acyloxazolidone intermediate using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted gamma-lactones.

AB - A versatile approach for the enantioselective synthesis of functionalised beta-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 the acyloxazolidone intermediate using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted gamma-lactones.

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U2 - 10.1039/b419492f

DO - 10.1039/b419492f

M3 - Article

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EP - 1728

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 9

ER -

Assembly intermediates in polyketide biosynthesis; enantioselective syntheses of beta-hydroxycarbonyl compounds

Abstract

ASJC Scopus subject areas

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