Total synthesis of spiruchostatin B aided by an automated synthesizer

Shinichiro Fuse; Kumiko Okada; Yusuke Iijima; Asami Munakata; Kazuhiro MacHida; Takashi Takahashi; Motoki Takagi; Kazuo Shin-Ya; Takayuki Doi

doi:10.1039/c0ob01169j

Total synthesis of spiruchostatin B aided by an automated synthesizer

Shinichiro Fuse, Kumiko Okada, Yusuke Iijima, Asami Munakata, Kazuhiro MacHida, Takashi Takahashi, Motoki Takagi, Kazuo Shin-Ya, Takayuki Doi

PHA - Molecular Pharmaceutical Science

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

34 Citations (Scopus)

Abstract

The total synthesis of a natural product HDAC inhibitor, spiruchostatin B, was successfully achieved. A 5-step synthesis that included an asymmetric aldol reaction was carried out in an automated synthesizer to provide an (E)-(S)-3-hydroxy-7-thio-4-heptenoic acid segment that is the crucial structure of cysteine-containing, depsipeptidic natural products such as spiruchostatins, FK228, FR901375, and largazole for their inhibitory activity against HDACs.

Original language	English
Pages (from-to)	3825-3833
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	10
DOIs	https://doi.org/10.1039/c0ob01169j
Publication status	Published - 2011 May 21

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AU - Fuse, Shinichiro

AU - Okada, Kumiko

AU - Iijima, Yusuke

AU - Munakata, Asami

AU - MacHida, Kazuhiro

AU - Takahashi, Takashi

AU - Takagi, Motoki

AU - Shin-Ya, Kazuo

AU - Doi, Takayuki

PY - 2011/5/21

Y1 - 2011/5/21

N2 - The total synthesis of a natural product HDAC inhibitor, spiruchostatin B, was successfully achieved. A 5-step synthesis that included an asymmetric aldol reaction was carried out in an automated synthesizer to provide an (E)-(S)-3-hydroxy-7-thio-4-heptenoic acid segment that is the crucial structure of cysteine-containing, depsipeptidic natural products such as spiruchostatins, FK228, FR901375, and largazole for their inhibitory activity against HDACs.

AB - The total synthesis of a natural product HDAC inhibitor, spiruchostatin B, was successfully achieved. A 5-step synthesis that included an asymmetric aldol reaction was carried out in an automated synthesizer to provide an (E)-(S)-3-hydroxy-7-thio-4-heptenoic acid segment that is the crucial structure of cysteine-containing, depsipeptidic natural products such as spiruchostatins, FK228, FR901375, and largazole for their inhibitory activity against HDACs.

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JO - Organic and Biomolecular Chemistry

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Total synthesis of spiruchostatin B aided by an automated synthesizer

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