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A Biomimetic Approach For Bicyclic Alkaloids Using Acetal Pro-nucleophile: Total Synthesis of (±)-Epilupinine and Formal Syntheses of (±)-Laburnine, (±)-Isoretronecanol (±)-Tashiromine†

IR@CDRI: CSIR-Central Drug Research Institute, Lucknow

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Field Value
 
Creator Koley, Dipankar
Srinivas, Kyatham
Krishna, Yarkali
Gupta, Archita
 
Date 2014-07-31T10:24:07Z
2014-07-31T10:24:07Z
2014
 
Identifier RSC Advances, 2014, 4, 3934-3937
http://hdl.handle.net/123456789/1326
 
Description A direct Mannich type diastereoselective biomimetic cyclization using acetal as pro-nucleophile leading to the hydroxymethyl substituted bicyclic framework of various bicyclic alkaloids is presented. Following this protocol, total synthesis of (±)-epilupinine and formal syntheses of (±)-laburnine, (±)-isoretronecanol and (±)-tashiromine are described.
 
Format 125728 bytes
application/pdf
 
Language es
 
Relation CSIR-CDRI Communication No. 8575
 
Subject Biomimetic Approach
Bicyclic
Alkaloids; Acetal Pro-nucleophile
Epilupinine
Laburnine
Isoretronecanol
Tashiromine
 
Title A Biomimetic Approach For Bicyclic Alkaloids Using Acetal Pro-nucleophile: Total Synthesis of (±)-Epilupinine and Formal Syntheses of (±)-Laburnine, (±)-Isoretronecanol (±)-Tashiromine†
 
Type Article