STEREOSELECTIVE TOTAL SYNTHESES OF (±)-RECIFEIOLIDE AND (<i>R</i>)-(+)-RICINELAIDIC ACID LACTONE
作者:Koichi Narasaka、Masahiko Yamaguchi、Teruaki Mukaiyama
DOI:10.1246/cl.1977.959
日期:1977.8.5
naturally occurring macrolide, (±)-recifeiolide, was synthesized stereoselectively. (E)-11-Hydroxy-8-dodecenoic acid (5) was obtained stereoselectively from 11-hydroxy-8-dodecynoic acid by the reduction with lithium, and the acid (5) was cyclized to (±)-recifeiolide in excellent yield via its 6-phenyl-2-pyridyl ester. Similarly, (R)-(+)-ricinelaidic acid was lactonized to afford the corresponding lactone
天然存在的大环内酯 (±)-recifeiolide 是立体选择性合成的。(E)-11-羟基-8-十二碳烯酸(5)是由11-羟基-8-十二碳烯酸通过锂还原立体选择性地获得,酸(5)环化为(±)-recifeiolide,收率极好通过其 6-苯基-2-吡啶酯。类似地,(R)-(+)-蓖麻油酸被内酯化以高产率提供相应的内酯。