Literature DB >> 15957925

New synthetic route for the enantioselective total synthesis of salinosporamide A and biologically active analogues.

Leleti Rajender Reddy1, Jean-François Fournier, B V Subba Reddy, E J Corey.   

Abstract

[reaction: see text] A total synthesis of the salinosporamide analogue 3 is described that starts with the novel cyclization 4 --> 5.

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Year:  2005        PMID： 15957925     DOI： 10.1021/ol0508734

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 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.  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

3.  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

4.  Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization.

Authors:  Justin R Struble; Jeffrey W Bode
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

5.  A(1,3)-strain enabled retention of chirality during bis-cyclization of beta-ketoamides: total synthesis of (-)-salinosporamide A and (-)-homosalinosporamide A.

Authors:  Henry Nguyen; Gil Ma; Daniel Romo
Journal:  Chem Commun (Camb)       Date:  2010-05-25       Impact factor: 6.222

6.  Concise total synthesis of (+/-)-salinosporamide A, (+/-)-cinnabaramide A, and derivatives via a bis-cyclization process: implications for a biosynthetic pathway?

Authors:  Gil Ma; Henry Nguyen; Daniel Romo
Journal:  Org Lett       Date:  2007-05-04       Impact factor: 6.005

Review 7.  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

8.  (S)-4-Trimethylsilyl-3-butyn-2-ol as an auxiliary for stereocontrolled synthesis of salinosporamide analogs with modifications at positions C2 and C5.

Authors:  Landy K Blasdel; DongEun Lee; Binyuan Sun; Andrew G Myers
Journal:  Bioorg Med Chem Lett       Date:  2013-09-30       Impact factor: 2.823

9.  (-)-Homosalinosporamide A and Its Mode of Proteasome Inhibition: An X-ray Crystallographic Study.

Authors:  Michael Groll; Henry Nguyen; Sreekumar Vellalath; Daniel Romo
Journal:  Mar Drugs       Date:  2018-07-19       Impact factor: 5.118

10.  Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors.

Authors:  Grace E Hubbell; Jetze J Tepe
Journal:  RSC Chem Biol       Date:  2020-09-16
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