An enantio-and diastereocontrolled synthesis of (-)-salinosporamide A

Yosuke Sato; Hayato Fukuda; Masaki Tomizawa; Tomohito Masaki; Masatoshi Shibuya; Naoki Kanoh; Yoshiharu Iwabuchi

doi:10.3987/COM-10-12042

An enantio-and diastereocontrolled synthesis of (-)-salinosporamide A

Yosuke Sato, Hayato Fukuda, Masaki Tomizawa, Tomohito Masaki, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

Tohoku University

Research output: Contribution to journal › Review article › peer-review

18 Citations (Scopus)

Abstract

The enantio-and diastereocontrolled total synthesis of (-)-salinosporamide A, a potent 20S proteasome inhibitor, was accomplished through organocatalytic aldolization, diastereoselective Claisen condensation, a Rh-catalyzed Reformatsky reaction, and an AZADO-catalyzed oxidative β-lactonization reaction as the key reactions.

Original language	English
Pages (from-to)	2239-2246
Number of pages	8
Journal	Heterocycles
Volume	81
Issue number	10
DOIs	https://doi.org/10.3987/COM-10-12042
Publication status	Published - 2010

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abstract = "The enantio-and diastereocontrolled total synthesis of (-)-salinosporamide A, a potent 20S proteasome inhibitor, was accomplished through organocatalytic aldolization, diastereoselective Claisen condensation, a Rh-catalyzed Reformatsky reaction, and an AZADO-catalyzed oxidative β-lactonization reaction as the key reactions.",

author = "Yosuke Sato and Hayato Fukuda and Masaki Tomizawa and Tomohito Masaki and Masatoshi Shibuya and Naoki Kanoh and Yoshiharu Iwabuchi",

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AU - Sato, Yosuke

AU - Fukuda, Hayato

AU - Tomizawa, Masaki

AU - Masaki, Tomohito

AU - Shibuya, Masatoshi

AU - Kanoh, Naoki

AU - Iwabuchi, Yoshiharu

PY - 2010

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AB - The enantio-and diastereocontrolled total synthesis of (-)-salinosporamide A, a potent 20S proteasome inhibitor, was accomplished through organocatalytic aldolization, diastereoselective Claisen condensation, a Rh-catalyzed Reformatsky reaction, and an AZADO-catalyzed oxidative β-lactonization reaction as the key reactions.

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An enantio-and diastereocontrolled synthesis of (-)-salinosporamide A

Abstract

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