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Efavirenz

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Signposts to Chiral Drugs

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Abstract

Biological target: Efavirenz is a non-nucleoside analogue, direct inhibitor of reverse transcriptase (RT) and thus blocks the transcription of human immunodeficiency virus-1 (HIV-1) viral RNA into the genome of infected cells. The binding at the active site of RT involves unique steric interactions.

Therapeutic profile: The drug is a first choice therapy for patients with HIV-1 infection.

Synthetic highlights: The initial step in the synthetic pathway to efavirenz involves the asymmetric addition of an alkyne anion to the ketone C=O bond. The generation of chiral Li+ aggregates elegantly determines the stereoselectivity of the reaction. Scale-up of alkynylation is promoted by the use of Et2Zn as a weak Lewis acid.

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Authors and Affiliations

  1. Faculty of Natural Sciences and Mathematics Department of Organic Chemistry, University of Zagreb, Horvatovac 102A, HR-10000, Zagreb, Croatia

    Prof. Dr. Vitomir Šunjić

  2. Research and Clinical Immunology Departments, University Hospital for Infectious Diseases “Dr. Fran Mihaljevic”, Mirogojska cesta 8, HR-10000, Zagreb, Croatia

    Prof. Dr. Michael J. Parnham

Authors
  1. Prof. Dr. Vitomir Šunjić
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  2. Prof. Dr. Michael J. Parnham
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Correspondence to Vitomir Šunjić .

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Šunjić, V., Parnham, M.J. (2011). Efavirenz. In: Signposts to Chiral Drugs. Springer, Basel. https://doi.org/10.1007/978-3-0348-0125-6_13

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