Total syntheses of cryptofolione were accomplished by two different
routes via a common intermediate that underwent a cross-metathesis
(CM) reaction with a vinyl lactone. The intermediate was prepared
by coupling of an acyl anion equivalent with a chiral allyl epoxide
synthon, or by Prins cyclization of a trans-cinnamaldehyde
with a chiral homoallylic alcohol. Goniothalamin was obtained as
a cross-metathesis product of the diacetate and vinyl lactone.
lactones - total synthesis - heterocycles - cyclizations - cryptofolione
