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

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JournalOrganic and Biomolecular Chemistry
DateE-pub ahead of print - 20 Aug 2012
DatePublished (current) - 14 Oct 2012
Issue number38
Volume10
Number of pages3
Pages (from-to)7666-8
Early online date20/08/12
Original languageEnglish

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.

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