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1Asymmetric syntheses of (8R,8aS)- and (8R,8aR)-8-hydroxy-5-indolizidinones:Two promising oxygenated indolizidine building blocks显示文摘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).ZHANG HongKui LI Xin HUANG Huang HUANG PeiQiang 2011Science China Chemistry2011,54,5:2
2(8R,8aS)-及(8R,8aR)-8-羟基-5-吲哚里西啶酮的不对称合成:两个有用的羟基吲哚里西啶合成砌块显示文摘以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.张洪奎 李欣 黄璜 黄培强 2011中国科学:化学2011,41,4:0
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