摘要
以3-苄氧基哌啶-2,6-二酮衍生物20为起始原料,分别合成了两类新的合成砌块(8R,8aS)-及(8R,8aR)-8-羟基-5-吲哚里西啶酮19a/19b和15a/15b.19a/19b的合成是基于反式非对映立体选择性还原烷基化反应(dr=93:7),接着经4步转化而成;而化合物15a/15b的制备则以双烯29的RCM反应为关键步骤,再经顺式立体选择性催化氢化(dr=91:9)反应完成.此外,还原化合物15a得到了(8R,8aR)-8-羟基-5-吲哚里西啶18.
Starting from the oxygenated piperidine building block 20,two synthetic approaches to new building blocks（8R,8aS） -and（8R,8aR） -8-hydroxy-5-indolizidinones 19a/19b and 15a/15b have been developed,respectively. The first one is based on the trans-diastereoselective reductive alkylation（dr=93：7） ,followed by a four-step procedure;and the second one called for the RCM reaction on the N,O-acetal derived from a vinylation,which was followed by a pyrrole formation,and a stereocontrolled cis-selective（dr=91：9） catalytic hydrogenation.Reduction of the diastereomer 15a produced（8R,8aR） -8-indolizidinol（18）.
出处
《中国科学：化学》
CAS
CSCD
北大核心
2011年第4期732-740,共9页
SCIENTIA SINICA Chimica
基金
国家自然科学基金(20672089,20832005)
国家基础科学人才培养基金(J1030415)
国家重点基础研究发展计划(973项目,2010CB833200)的资助
