The thiopyran route to polypropionates

Dale E. Ward

doi:10.1039/C1CC13323C

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Chemical Communications

Issue 41, 2011

Urgent high quality communications from across the chemical sciences.

Impact Factor 6.169 100 Issues per Year Indexed in MEDLINE

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The thiopyran route to polypropionates

Dale E. Ward*^a

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Department of Chemistry, University of Saskatchewan, Saskatoon, Canada
E-mail: dale.ward@usask.ca ;
Fax: 306-966-4730 ;
Tel: 306-966-4656

Chem. Commun., 2011,47, 11375-11393

DOI: 10.1039/C1CC13323C
Received 04 Jun 2011, Accepted 23 Jun 2011
First published online 15 Jul 2011

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Abstract
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The strategic use of thiopyran templates to facilitate polypropionate synthesis was first demonstrated in Woodward's landmark total synthesis of erythromycin A in 1981 where the topology of a fused bicyclic system was exploited. In the ensuing three decades, various alternative strategic applications of thiopyran motifs to achieve key stereoselective transformations have emerged including, inter alia, unique substrates for chemoenzymatic syntheses, surrogates for 3-pentanone in enantioselective aldol reactions, and templates for enantiotopic group selective reactions. This review summarizes these developments.

Abstract from Natural Product Updates 2012

A review, with 92 references, on the synthesis of polypropionates from thiopyran, including the total syntheses of various natural products.

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