An enantioselective synthesis of voriconazole

Keiji Tamura; Makoto Furutachi; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/jo4019528

An enantioselective synthesis of voriconazole

Keiji Tamura, Makoto Furutachi, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

A new seven-step sequence to access voriconazole, a clinically used antifungal agent, was developed. The initial catalytic asymmetric cyanosilylation is the key to constructing the consecutive tetra- and trisubstituted stereogenic centers. The fluoropyrimidine unit frequently triggered unexpected side reactions, but careful amendment of the reaction sequence allowed for the concise enantioselective synthesis.

Original language	English
Pages (from-to)	11396-11403
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	78
Issue number	22
DOIs	https://doi.org/10.1021/jo4019528
Publication status	Published - 2013 Nov 15
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo4019528

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title = "An enantioselective synthesis of voriconazole",

abstract = "A new seven-step sequence to access voriconazole, a clinically used antifungal agent, was developed. The initial catalytic asymmetric cyanosilylation is the key to constructing the consecutive tetra- and trisubstituted stereogenic centers. The fluoropyrimidine unit frequently triggered unexpected side reactions, but careful amendment of the reaction sequence allowed for the concise enantioselective synthesis.",

author = "Keiji Tamura and Makoto Furutachi and Naoya Kumagai and Masakatsu Shibasaki",

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AU - Tamura, Keiji

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AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

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Y1 - 2013/11/15

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AB - A new seven-step sequence to access voriconazole, a clinically used antifungal agent, was developed. The initial catalytic asymmetric cyanosilylation is the key to constructing the consecutive tetra- and trisubstituted stereogenic centers. The fluoropyrimidine unit frequently triggered unexpected side reactions, but careful amendment of the reaction sequence allowed for the concise enantioselective synthesis.

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An enantioselective synthesis of voriconazole

Abstract

ASJC Scopus subject areas

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