Total Synthesis of Chatenaytrienins-1, -3 and -4 and Muridienins-1–4 Enabled by C(sp)–C(sp3) Sonogashira Coupling

Abstract

A concise and efficient protecting-group-free total synthesis of chatenaytrienins-1, -3, -4 and muridienins-1-4 have been achieved. The key steps involved ring-closing metathesis (RCM) and C(sp)-C(sp3)-Sonogashira coupling. In this paper we have achieved the first total synthesis of chatenaytrienin-3 and muridienins-1-4 in 7 linear steps and high overall yields. Further, this strategy can be explored to synthesize various bis-methylene-interrupted polyunsaturated natural compounds having 1,5- or 1,5,9,n-(Z)-configured double bonds, epoxide or hydroxy groups.