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Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan

Authors :
Trzupek, John D.
Dongjoo Lee
Crowley, Brendan M.
Marathias, Vasilios M.
Danishefsky, Samuel J.
Source :
Journal of the American Chemical Society. June 23, 2010, Vol. 132 Issue 24, 8506-8512
Publication Year :
2010

Abstract

2-Substituted derivative of L-tryptophan has undergone conversion to a prephalarine structure in a single step. The reaction has occurred in a diastereoselective fashion, which has led to the naturally occurring version of the alkaloid phalarine.

Details

Language :
English
ISSN :
00027863
Volume :
132
Issue :
24
Database :
Gale General OneFile
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
edsgcl.231658632