Synthesis of New 7,13-Dithiaprostaglandins

Abstract

Much attention has been paid to heteroprostaglandins focusing on their different biological activities from those of the naturally occurring prostaglandins or other kinds of chemically modified prostanoic acids. Many laboratories have succeeded in the syntheses of 3-thia,¹ 7-thia,² 9-thia,³ 11-thia,⁴ 13-thia,⁵ 3-oxa,^1,6 7-oxa,⁷ 9-oxa,⁸ 10-oxa,⁹ 11-oxa,¹⁰ 8-aza,¹¹ 9-aza,¹² 12-aza,¹³ 9,11-dioxa,^14,15 9,11-dithia,¹⁵ 8,12-diaza,¹⁶ 9-aza-11-thia,^17,18 and 9-aza-11-oxa¹⁸ prostanoids. Some of these heteroprostaglandins showed selective agonistic or antagonistic activities¹⁹ separating some biological activitites from undesired side-effects encountered in naturally occurring prostaglandins. Our laboratory has recently reported a synthesis of E-type 7-thiaprostaglandins from a new key intermediate, sulfur containing cyclopentenone derivative 3.²⁰