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Title: Total synthesis of entecavir
Author: Velasco Turbau, Javier
Ariza Piquer, Xavier
Badía, Laura
Bartra, Martí
Berenguer, Ramon
Farràs i Soler, Jaume
Gallardo, Joan
García Gómez, Jordi
Gasanz, Yolanda
Keywords: Hepatitis B
Medicaments antivírics
Reacció aldòlica
Àcids nucleics
Hepatitis B
Antiviral agents
Aldol reaction
Nucleic acids
Issue Date: 2013
Publisher: American Chemical Society
Abstract: Entecavir (BMS-200475) was synthesized from 4-trimethylsilyl-3-butyn-2-one and acrolein. The key features of its preparation are: (i) a stereoselective boron-aldol reaction to afford the acyclic carbon skeleton of the methylenecylopentane moiety; (ii) its cyclization by a Cp2TiCl-catalyzed intramolecular radical addition of an epoxide to an alkyne; and (iii) the coupling with a purine derivative by a Mitsunobu reaction.
Note: Versió postprint del document publicat a:
It is part of: Journal of Organic Chemistry, 2013, vol. 78, num. 11, p. 5482-5491
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ISSN: 0022-3263
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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