Asymmetric Synthesis of (-)-Lentiginosine by Double Aza-Michael Reaction

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/50678

Title:	Asymmetric Synthesis of (-)-Lentiginosine by Double Aza-Michael Reaction
Authors:	Liu,SW;Hsu,HC;Chang,CH;Tsai,HHG;Hou,DR
Contributors:	化學學系
Keywords:	NATURALLY-OCCURRING IMINOSUGARS;CONCISE TOTAL-SYNTHESIS;STEREOSELECTIVE-SYNTHESIS;POLYHYDROXYLATED ALKALOIDS;GLYCOSIDASE INHIBITORS;D-GLUCOSE;QUINOLIZIDINE ALKALOIDS;ABSOLUTE-CONFIGURATION;PYRROLIZIDINIC ANALOG;BIOLOGICAL-ACTIVITY
Date:	2010
Issue Date:	2012-03-27 18:07:43 (UTC+8)
Publisher:	國立中央大學
Abstract:	Total synthesis of (-)-lentiginosine (1) was achieved in nine steps from (3R, 4R)-3,4-dihydroxy-1,5-hexadiene (2). Cross metathesis, vinyl addition and DDQ oxidation were applied to generate the key 3-oxonona-1,4,8-triene 6, which was cyclised to 4-oxopiperidine 7 by diastereoselective double aza-Michael reaction. Both theoretical and empirical studies support that the stereochemical assignment of the major Michael adduct is the desired (2R)-4-oxopiperidine 7.
Relation:	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Appears in Collections:	[Department of Chemistry] journal & Dissertation

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