A general approach toward bakkanes: short synthesis of (+/-)-bakkenolide-a (fukinanolide).
[reaction: see text] An efficient, general, and fully stereocontrolled approach to the family of bakkanes is disclosed. This route highlights a highly diastereoselective Diels-Alder/aldol sequence to furnish the common hydrindane precursor for the synthesis of bakkanes. The projected common intermediate was transformed to the (+/-)-bakkenolide-A in a short sequence.
Reddy
D Srinivasa
DS
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Malott Hall, Lawrence, Kansas 66045-7582, USA. dsreddy88@yahoo.com
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002384:Catalysis; D015394:Molecular Structure; D036901:Petasites / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D012717:Sesquiterpenes; D015107:4-Butyrolactone; C016257:bakkenolide A