Aj. Sanchez et Jp. Konopelski, PHENOL BENZYLIC EPOXIDE TO QUINONE METHIDE ELECTRON REORGANIZATION - SYNTHESIS OF (+ -)-TAXODONE/, Journal of organic chemistry, 59(18), 1994, pp. 5445-5452
The total synthesis of(+/-)-taxodone (1) is described. The C-ring is f
ormed by the cycloaddition of methyl acrylate with furan 8, the latter
derived from isodrimenin. The C13 isopropyl group was introduced via
a sulfur ylide rearrangement followed by reductive cleavage. Compound
I was synthesized in 61% yield by deprotection and intramolecular oxir
ane opening of diacetate 31 with potassium tert-butoxide and water in
THF.