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]