A New Prostaglandin Synthon from the 4-Oxatricyclo [4. 3. 0. 0^{3, 7}] non-8-ene System. A Total Synthesis of (±)-Prostaglandin F_2a

Abstract

The synthesis of a new prostaglandin synthon (14) from 5-trichloromethyl-4-oxatricyclo [4. 3. 0. 0^{3, 7}] non-8-ene (2) and its conversion to prostaglandin F_2α (21) are described. Compound (2) was transformed into the acetylene derivative (5) which was then led to the C-9 acetylene lactone (14) via a 6-step, 8-stage reaction. A new synthesis of (±)-prostaglandin F_2a (21) was completed through a 5-step reaction starting from the C-9 lactone (14).