An efficient asymmetric synthesis of prostaglandin E1

An asymmetric total synthesis of Prostaglandin E-1 (5) has been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from furan with 96% ee. The key reaction step was a kinetic enzymatic resolution followed by an in situ inversion. A catalytic asymmetric reduction of the gamma-iodo vinyl ketone 19 with the Corey CBS catalyst gave the omega-side chain 7 with >96% ee. Conjugate addition using the reaction with dilithiocyanocuprate followed by mild cleavage of the silyl protective groups and enzymatic hydrolysis of the methyl ester 22 gave (-)-PGE(1) 5 in high yield.