Literature DB >> 17441136

Total synthesis of lactacystin and salinosporamide A.

Masakatsu Shibasaki1, Motomu Kanai, Nobuhisa Fukuda.   

Abstract

Lactacystin and salinosporamide A are fascinating molecules with regard to both their chemical structures and biological activities. These naturally occurring compounds are potent and selective proteasome inhibitors. The molecular structures are characterized by their densely functionalized gamma-lactam cores. The structure and biological properties of these two compounds are attracting the attention of many chemists as challenging synthetic targets. We discuss their synthetic strategies in this review.

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Year:  2007        PMID: 17441136     DOI: 10.1002/asia.200600310

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  10 in total

Review 1.  Salinosporamide natural products: Potent 20 S proteasome inhibitors as promising cancer chemotherapeutics.

Authors:  Tobias A M Gulder; Bradley S Moore
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

2.  Highly diastereo- and enantioselective additions of homoenolates to nitrones catalyzed by N-heterocyclic carbenes.

Authors:  Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2008-01-31       Impact factor: 15.419

Review 3.  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

4.  Bioinspired total synthesis and human proteasome inhibitory activity of (-)-salinosporamide A, (-)-homosalinosporamide A, and derivatives obtained via organonucleophile promoted bis-cyclizations.

Authors:  Henry Nguyen; Gil Ma; Tatiana Gladysheva; Trisha Fremgen; Daniel Romo
Journal:  J Org Chem       Date:  2010-11-03       Impact factor: 4.354

5.  Total Synthesis of (-)-Salinosporamide A via a Late Stage C-H Insertion.

Authors:  Hadi Gholami; Aman Kulshrestha; Olivia K Favor; Richard J Staples; Babak Borhan
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-10       Impact factor: 15.336

6.  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

7.  Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.

Authors:  Christian M Chaheine; Conner J Song; Paul T Gladen; Daniel Romo
Journal:  Organic Synth       Date:  2021

Review 8.  Generating a generation of proteasome inhibitors: from microbial fermentation to total synthesis of salinosporamide a (marizomib) and other salinosporamides.

Authors:  Barbara C Potts; Kin S Lam
Journal:  Mar Drugs       Date:  2010-03-25       Impact factor: 5.118

9.  Function-oriented biosynthesis of beta-lactone proteasome inhibitors in Salinispora tropica.

Authors:  Markus Nett; Tobias A M Gulder; Andrew J Kale; Chambers C Hughes; Bradley S Moore
Journal:  J Med Chem       Date:  2009-10-08       Impact factor: 7.446

10.  Construction of Polycyclic γ-Lactams and Related Heterocycles via Electron Catalysis.

Authors:  Jun Xuan; Constantin G Daniliuc; Armido Studer
Journal:  Org Lett       Date:  2016-11-29       Impact factor: 6.005

  10 in total

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