Issue 10, 2011
From the journal:

Organic & Biomolecular Chemistry

Total synthesis of spiruchostatin B aided by an automated synthesizer†

Shinichiro Fuse,a   Kumiko Okada,a   Yusuke Iijima,a   Asami Munakata,b   Kazuhiro Machida,c   Takashi Takahashi,*a   Motoki Takagi,b   Kazuo Shin-yad  and  Takayuki Doi*e  

* Corresponding authors

a Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, Japan
E-mail: ttak@apc.titech.ac.jp
Fax: +81-3-5734-2884
Tel: +81-3-5734-2120

b Japan Biological Informatics Consortium (JBIC), 2-4-7, Aomi, Koto-ku, Tokyo, Japan

c Development Department, ChemGenesis Incorporated; 4-10-1, Nihonbashi-honcho, Chuo-ku, Tokyo, Japan

d National Institute of Advanced Industrial Science and Technology, 2-4-7, Aomi, Koto-ku, Tokyo, Japan

e Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba, Sendai, Japan
E-mail: doi_taka@mail.pharm.tohoku.ac.jp
Fax: +81-22-795-6864
Tel: +81-22-795-6865

Abstract

The total synthesis of a natural productHDAC 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.

Graphical abstract: Total synthesis of spiruchostatin B aided by an automated synthesizer

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Article information

DOI
https://doi.org/10.1039/C0OB01169J
Article type
Paper
Submitted
13 Dec 2010
Accepted
28 Feb 2011
First published
29 Mar 2011

Org. Biomol. Chem., 2011,9, 3825-3833

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Total synthesis of spiruchostatin B aided by an automated synthesizer

S. Fuse, K. Okada, Y. Iijima, A. Munakata, K. Machida, T. Takahashi, M. Takagi, K. Shin-ya and T. Doi, Org. Biomol. Chem., 2011, 9, 3825 DOI: 10.1039/C0OB01169J

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