A concise flow synthesis of Efavirenz

Correia, Camille A.; Gilmore, Kerry; McQuade, D. Tyler; Seeberger, Peter H.

doi:10.1002/anie.201411728

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A concise flow synthesis of Efavirenz

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Correia, Camille A.
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Gilmore, Kerry
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger, Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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引用

Correia, C. A., Gilmore, K., McQuade, D. T., & Seeberger, P. H. (2015). A concise flow synthesis of Efavirenz. Angewandte Chemie International Edition, 54(16), 4945-4948. doi:10.1002/anie.201411728.

引用: https://hdl.handle.net/11858/00-001M-0000-0027-1250-1

要旨

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.