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Paper | Regular issue | Vol 36, No. 10, 1993, pp.2345-2366
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6465
Photocyclization of Enamides. 38. Reductive Photocyclization of α-(Methylthio)- and α-(Arylthio)enamides

Takeaki Naito,* Hiromi Tanada, Yumiko Suzuki, Haruko Saito, Toshiko Kiguchi, and Ichiya Ninomiya

*Kobe Women's College of Pharmacy, Motoyamakita, Higashinada, Kobe 658-8558, Japan

Abstract

Reductive photocyclization of α-(methylthio)enamide (2) gave exclusively six-membered lactams (3) and (4) while the same reaction of α-(arylthio)enamides (6) and (12) was found to afford five-membered lactams (7) and (13) as major proucts. A novel total synthesis of (±)-polyzonimine (18b) was accomplished by applying the newly found reductive photocyclization of α-(naphthylthio)enemide leading to the formation of five-membered lactams.