Total synthesis of the novel antifungal agent (+/-)-jesterone.
A total synthesis of the novel, biologically active epoxyquinone natural product (+/-)-jesterone has been accomplished from the readily accessible Diels-Alder adduct of cyclopentadiene and prenylated-p-benzoquinone. The approach delineated here is notable for its conceptual simplicity and efficient orchestration of a series of chemo-, regio-, and stereoselective operations. [reaction: see text]
Mehta
Goverdhan
G
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
Pan
Subhas Chandra
SC
D000475:Alkenes / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D000935:Antifungal Agents; D004852:Epoxy Compounds; C431025:jesterone