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

David J Burns, Shuji Hachisu, Peter O'Brien, Richard J K Taylor

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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.
Original languageEnglish
Pages (from-to)7666-8
Number of pages3
JournalOrganic and Biomolecular Chemistry
Issue number38
Early online date20 Aug 2012
Publication statusPublished - 14 Oct 2012

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