Literature DB >> 29711503

An Efficient and Concise Enantioselective Total Synthesis of Lactacystin.

E J Corey1, Weidong Li1, Tohru Nagamitsu1.   

Abstract

A selective, irreversible inhibitor of proteasome function, lactacystin (1) is an important experimental tool in cell biology. An efficient and direct enantioselective synthesis of lactacystin proceeds via the intermediates shown below. This process allows for the first time easy access to analogues of lactacystin in which the isopropyl substituent is replaced by other lipophilic groups. PMB=p-methoxybenzyl. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Enzyme inhibitors; Lactacystin; Lactones; Stereocontrol; Total synthesis

Year:  1998        PMID: 29711503     DOI: 10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

Review 1.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

2.  Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin.

Authors:  Wenxin Gu; Richard B Silverman
Journal:  J Org Chem       Date:  2011-09-27       Impact factor: 4.354

3.  Formal synthesis of (+)-lactacystin from l-serine.

Authors:  Philip C Bulman Page; Ross L Goodyear; Yohan Chan; Alexandra M Z Slawin; Steven M Allin
Journal:  RSC Adv       Date:  2019-09-24       Impact factor: 4.036

4.  Development of Small Molecular Proteasome Inhibitors Using a Caenorhabditis elegans Screen.

Authors:  Sudhir Nayak; Michela Fiaschi; Dana King; Erica R Tabakin; Lyndsay Wood; David A Hunt
Journal:  Int J Med Chem       Date:  2014-11-11
  4 in total

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