Total synthesis of prostaglandin-F2? through homoconjugate addition of an organocuprate reagent to a tricyclo[3.2.0.02,7]heptanone

Abstract

Prostaglandin-F2α has been synthesised from cyclopentadiene in a highly stereoselective ten-step sequence of reactions. The key step involves the coupling of a protected 3-hydroxyoct-1-enyl unit to 3-dimethyl-t-butylsilyloxytricyclo[3.2.0.02,7]heptan-6-one through the use of a mixed organocuprate reagent.