Asymmetric syntheses of (8R,8aS)- and (8R,8aR)-8-hydroxy-5-indolizidinones:Two promising oxygenated indolizidine building blocks |
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| Authors: | ZHANG HongKui LI Xin HUANG Huang & HUANG PeiQiang |
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| Affiliation: | ZHANG HongKui,LI Xin,HUANG Huang & HUANG PeiQiang Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen. China |
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| Abstract: | 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:... |
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| Keywords: | indolizidines building blocks diastereoselective synthesis RCM reaction catalytic hydrogenation |
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