Synthesis of (−) cephalosporolide E and (+) cephalosporolide F utilizing the vinylogous Mukaiyama type reaction with an α-chloro sulfide†,10.1039/C6RA13861F

热搜：

Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Synthesis of (−) cephalosporolide E and (+) cephalosporolide F utilizing the vinylogous Mukaiyama type reaction with an α-chloro sulfide†

K. V. S. Ramakrishna

RSC Advances Pub Date : 07/27/2016 00:00:00 , DOI:10.1039/C6RA13861F

Abstract

The synthesis of cephalosporolide E and F is described utilizing diastereoselective reduction of a propargylic ketone using a Noyori catalyst to create the C6 carbinol stereogenic center. A vinylogous silylketene acetal addition to an α-chloro sulfide is exploited for stereoselective carbon–carbon bond formation and introduction of the butenolide moiety. Oxidative radical cyclization is utilized for the creation of the [5,5]-spiroketal moiety.