Literature DB >> 21445425

Total synthesis of spiruchostatin B aided by an automated synthesizer.

Shinichiro Fuse1, Kumiko Okada, Yusuke Iijima, Asami Munakata, Kazuhiro Machida, Takashi Takahashi, Motoki Takagi, Kazuo Shin-ya, Takayuki Doi.   

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.

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Year:  2011        PMID: 21445425     DOI: 10.1039/c0ob01169j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  7 in total

Review 1.  An overview of naturally occurring histone deacetylase inhibitors.

Authors:  Bumki Kim; Jiyong Hong
Journal:  Curr Top Med Chem       Date:  2015       Impact factor: 3.295

Review 2.  The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Authors:  Melanie Trobe; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

3.  Samarium iodide-mediated Reformatsky reactions for the stereoselective preparation of β-hydroxy-γ-amino acids: synthesis of isostatine and dolaisoleucine.

Authors:  Christopher G Nelson; Terrence R Burke
Journal:  J Org Chem       Date:  2011-12-14       Impact factor: 4.354

4.  Automated synthesis of a library of triazolated 1,2,5-thiadiazepane 1,1-dioxides via a double aza-Michael strategy.

Authors:  Qin Zang; Salim Javed; David Hill; Farman Ullah; Danse Bi; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2012-08-01       Impact factor: 3.784

5.  Origin and bioactivities of thiosulfinated FK228.

Authors:  Xiangyang Liu; Grant C Currens; Liang Xue; Yi-Qiang Cheng
Journal:  Medchemcomm       Date:  2019-03-25       Impact factor: 3.597

6.  Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate.

Authors:  Hisashi Masui; Sae Yosugi; Shinichiro Fuse; Takashi Takahashi
Journal:  Beilstein J Org Chem       Date:  2017-01-17       Impact factor: 2.883

Review 7.  Case studies of the synthesis of bioactive cyclodepsipeptide natural products.

Authors:  Sara C Stolze; Markus Kaiser
Journal:  Molecules       Date:  2013-01-24       Impact factor: 4.411

  7 in total

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