Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesisElectronic supplementary information (ESI) available: Full experimental procedures and copies of 1H/13C NMR spectra and CSP-HPLC data. See DOI: 10.1039/c2ob26406d

Due to the lack of availability of unnatural (+)-quinic acid as a starting material, a 6-step synthesis of butane diacetal-protected (4 S ,5 S )-dihydroxycyclohexen-1-one (formally derived from (+)-quinic acid) has been devised. The key catalytic asymmetric step involves a chiral Co-salen-catalysed...

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Bibliographic Details
Main Authors Burns, David J, Hachisu, Shuji, O'Brien, Peter, Taylor, Richard J. K
Format Journal Article
LanguageEnglish
Published 12.09.2012
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Summary:Due to the lack of availability of unnatural (+)-quinic acid as a starting material, a 6-step synthesis of butane diacetal-protected (4 S ,5 S )-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. (4 S ,5 S )-Dihydroxycyclohexen-1-one was utilised in the synthesis of two cyclohexenone natural products isolated from the mycelia of Lasiodiplodia theobromae . A route to a butane diacetal-protected (4 S ,5 S )-dihydroxycyclohexen-1-one (formally derived from unavailable (+)-quinic acid) has been developed and utilised in the first synthesis of two cyclohexenone natural products.
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C NMR spectra and CSP-HPLC data. See DOI
H
10.1039/c2ob26406d
Electronic supplementary information (ESI) available: Full experimental procedures and copies of
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob26406d