Issue 38, 2012

Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis

Abstract

Due to the lack of availability of unnatural (+)-quinic acid as a starting material, a 6-step synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one (formally derived from (+)-quinic acid) has been devised. The key catalytic asymmetric step involves a chiral Co-salen-catalysed epoxide ring-opening reaction. (4S,5S)-Dihydroxycyclohexen-1-one was utilised in the synthesis of two cyclohexenone natural products isolated from the mycelia of Lasiodiplodia theobromae.

Graphical abstract: Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis

Supplementary files

Article information

Article type
Communication
Submitted
19 Jul 2012
Accepted
17 Aug 2012
First published
20 Aug 2012

Org. Biomol. Chem., 2012,10, 7666-7668

Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis

D. J. Burns, S. Hachisu, P. O'Brien and R. J. K. Taylor, Org. Biomol. Chem., 2012, 10, 7666 DOI: 10.1039/C2OB26406D

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