The total synthesis of (+/-)-taxodone (1) is described. The C-ring is
formed by the cycloaddition of methyl acrylate with siloxy-furan 5 der
ived from isodrimenin (4). The C13 isopropyl roup was introduced via a
sulfur ylide rearrangement followed by reductive cleavage. Compound 1
was synthesized in 61% yield from diacetate 18 by deprotection and in
tramolecular oxirane opening with potassium t-butoxide and water in TH
F.