Literature DB >> 17628106

First total synthesis of antitumor natural product (+)- and (-)-pericosine A: determination of absolute stereo structure.

Yoshihide Usami1, Isao Takaoka, Hayato Ichikawa, Yusuke Horibe, Syunsuke Tomiyama, Misako Ohtsuka, Yumi Imanishi, Masao Arimoto.   

Abstract

The first total synthesis of (+)- and (-)-pericosine A has been achieved, enabling the revision and determination of the absolute configuration of this antitumor natural product as methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate. Every step of this total synthesis proceeded well with excellent stereoselectivity. Structures of the intermediates in crucial steps were confirmed by detailed 2D NMR analysis.

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Year:  2007        PMID: 17628106     DOI: 10.1021/jo070715l

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

1.  Glaucocalyxin A inhibits the growth of liver cancer Focus and SMMC-7721 cells.

Authors:  Lisha Tang; Xiaofeng Jin; Xiaohui Hu; Xiaoding Hu; Zulong Liu; Long Yu
Journal:  Oncol Lett       Date:  2015-12-03       Impact factor: 2.967

Review 2.  Recent synthetic studies leading to structural revisions of marine natural products.

Authors:  Yoshihide Usami
Journal:  Mar Drugs       Date:  2009-07-13       Impact factor: 5.118

Review 3.  Discovery of natural product anticancer agents from biodiverse organisms.

Authors:  A Douglas Kinghorn; Young-Won Chin; Steven M Swanson
Journal:  Curr Opin Drug Discov Devel       Date:  2009-03

4.  Synthesis of Natural O-Linked Carba-Disaccharides, (+)- and (-)-Pericosine E, and Their Analogues as α-Glucosidase Inhibitors.

Authors:  Yoshihide Usami; Koji Mizuki; Rikiya Kawahata; Makio Shibano; Atsuko Sekine; Hiroki Yoneyama; Shinya Harusawa
Journal:  Mar Drugs       Date:  2017-01-23       Impact factor: 5.118

5.  Synthesis of novel seven-membered carbasugars and evaluation of their glycosidase inhibition potentials.

Authors:  Vignesh Athiyarath; Naveen J Roy; A T V Vijil; Kana M Sureshan
Journal:  RSC Adv       Date:  2021-03-02       Impact factor: 3.361

6.  Synthesis of 6-Halo-Substituted Pericosine A and an Evaluation of Their Antitumor and Antiglycosidase Activities.

Authors:  Yoshihide Usami; Yoshino Mizobuchi; Mai Ijuin; Takeshi Yamada; Mizuki Morita; Koji Mizuki; Hiroki Yoneyama; Shinya Harusawa
Journal:  Mar Drugs       Date:  2022-06-30       Impact factor: 6.085

7.  Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare.

Authors:  Yoshihide Usami; Hayato Ichikawa; Masao Arimoto
Journal:  Int J Mol Sci       Date:  2008-03-24       Impact factor: 6.208

  7 in total

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