Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2- naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor

Akio Ojida; Nobuyuki Matsunaga; Tomohiro Kaku; Akihiro Tasaka

doi:10.1016/j.tetasy.2004.02.035

Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2- naphthyl)-2-methylpropan-1-ol as a potent C_17,20-lyase inhibitor

Akio Ojida, Nobuyuki Matsunaga, Tomohiro Kaku, Akihiro Tasaka

Molecular Bioinformatics

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

7 Citations (Scopus)

Abstract

An efficient stereocontrolled synthesis of the potent C_17,20- lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1- propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale.

Original language	English
Pages (from-to)	1555-1559
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	15
Issue number	10
DOIs	https://doi.org/10.1016/j.tetasy.2004.02.035
Publication status	Published - May 24 2004

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2004.02.035

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title = "Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2- naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor",

abstract = "An efficient stereocontrolled synthesis of the potent C17,20- lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1- propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale.",

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AU - Ojida, Akio

AU - Matsunaga, Nobuyuki

AU - Kaku, Tomohiro

AU - Tasaka, Akihiro

PY - 2004/5/24

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AB - An efficient stereocontrolled synthesis of the potent C17,20- lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1- propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale.

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Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2- naphthyl)-2-methylpropan-1-ol as a potent C_17,20-lyase inhibitor

Abstract

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