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

TY - JOUR

T1 - Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis

AU - Burns, David J

AU - Hachisu, Shuji

AU - O'Brien, Peter

AU - Taylor, Richard J K

PY - 2012/10/14

Y1 - 2012/10/14

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84874849424&partnerID=8YFLogxK

U2 - 10.1039/c2ob26406d

DO - 10.1039/c2ob26406d

M3 - Article

C2 - 22930235

SN - 1477-0520

VL - 10

SP - 7666

EP - 7668

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 38

ER -