A concise flow synthesis of efavirenz

Angewandte Chemie
Camille A CorreiaPeter H Seeberger

Abstract

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.

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Citations

Jul 15, 2015·Organic Letters·Stefan MatthiesPeter H Seeberger
Apr 5, 2017·Annual Review of Chemical and Biomolecular Engineering·Jisong ZhangGuangsheng Luo
Jun 10, 2017·Nature Communications·Vincenza DragoneLeroy Cronin
Jan 21, 2017·Chemical Society Reviews·Joshua Britton, Colin L Raston
Sep 2, 2015·Chemical Communications : Chem Comm·Tomoya NobutaPeter H Seeberger
May 15, 2018·Angewandte Chemie·Robert E ZieglerTimothy F Jamison
Jun 8, 2018·Annual Review of Chemical and Biomolecular Engineering·Christopher L BurchamMartin D Johnson
Jun 7, 2018·Angewandte Chemie·Niels WeidmannPaul Knochel
Feb 1, 2018·Chemistry : a European Journal·Ping ZhangAndrea Adamo
Jul 8, 2017·Beilstein Journal of Organic Chemistry·Chinmay A Shukla, Amol A Kulkarni
Jan 31, 2017·Angewandte Chemie·Joshua BrittonGregory A Weiss
Apr 27, 2021·The Journal of Organic Chemistry·Alexandra SeemannAndreas Kirschning
Jun 2, 2021·The Journal of Organic Chemistry·Cloudius R SagandiraPaul Watts
Jun 17, 2021·Chemical Communications : Chem Comm·Yasunori TodaHiroyuki Suga
Dec 26, 2018·Journal of the American Chemical Society·Roozbeh YousefiJeffrey N Johnston
Dec 6, 2018·Journal of Medicinal Chemistry·Vigneshwaran NamasivayamSiddappa N Byrareddy

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