Asymmetric cyclopentannelation. Chiral auxiliary on the allene.
An enantioselective variant of the synthesis of cross-conjugated cyclopentenones, based on D-glucose-derived chiral auxiliaries, is described. Minor modification of the method makes it applicable to the preparation of both enantiomeric series of products. Both enantiomers of the key intermediate in our roseophilin synthesis have been prepared.
Harrington
P E
PE
Department of Chemistry, University of Hawai'i at Manoa, 2545 The Mall, Honolulu, Hawaii 96822, USA.
Tius
M A
MA
D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D003517:Cyclopentanes; D007202:Indicators and Reagents; C013905:cyclopentenone