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A Concise Flow Synthesis of Efavirenz
Author(s) -
Correia Camille A.,
Gilmore Kerry,
McQuade D. Tyler,
Seeberger Peter H.
Publication year - 2015
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.201411728
Subject(s) - efavirenz , intramolecular force , combinatorial chemistry , isocyanate , carbamate , yield (engineering) , human immunodeficiency virus (hiv) , chemistry , stereochemistry , medicine , organic chemistry , antiretroviral therapy , virology , materials science , viral load , metallurgy , polyurethane
Efavirenz is an essential medicine for the treatment of HIV, which is still inaccessible to millions of people worldwide. A novel, semi‐continuous process provides rac ‐Efavirenz with an overall yield of 45 %. This streamlined proof‐of‐principle synthesis relies on the efficient copper‐catalyzed formation of an aryl isocyanate and a subsequent intramolecular cyclization to install the carbamate core of Efavirenz in one step. The three‐step method represents the shortest synthesis of this life‐saving drug to date.