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

Research output: Contribution to journalArticlepeer-review

31 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 languageEnglish
Pages (from-to)3825-3833
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number10
DOIs
Publication statusPublished - 2011 May 21

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Total synthesis of spiruchostatin B aided by an automated synthesizer'. Together they form a unique fingerprint.

Cite this