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Protic‐Solvent‐Mediated Cycloisomerization of Quinoline and Isoquinoline Propargylic Alcohols: Syntheses of (±)‐3‐Demethoxyerythratidinone and (±)‐Cocculidine
Author(s) -
Heller Stephen T.,
Kiho Toshihiro,
Narayan Alison R. H.,
Sarpong Richmond
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201304687
Subject(s) - cycloisomerization , isoquinoline , quinoline , chemistry , erythrina , organic chemistry , solvent , combinatorial chemistry , stereochemistry , catalysis , botany , biology
Putting the “benz” in indolizinones : A cycloisomerization approach to benz[ g ]indolizinones and benz[ e ]indolizinones provides the first general route to these unique azacycles (see example). The utility of the benzindolizinone products was demonstrated by the application of this method to the total synthesis of the Erythrina alkaloids 3‐demethoxyerythratidinone and cocculidine.