An efficient asymmetric synthesis of prostaglandin E-1

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