Literature DB >> 17497868

Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052).

Taotao Ling1, Venkat R Macherla, Rama Rao Manam, Katherine A McArthur, Barbara C M Potts.   

Abstract

A novel enantioselective total synthesis of 20S proteasome inhibitor Salinosporamide A (NPI-0052; 1) is presented. Key features include intramolecular aldol cyclization of 6 to simultaneously generate the three chiral centers of advanced intermediate 5, cyclohexene ring addition using B-2-cyclohexen-1-yl-9-BBN, and inversion of the C-5 stereocenter by oxidation followed by enantioselective enzymatic reduction.

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Year:  2007        PMID： 17497868     DOI： 10.1021/ol0706051

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


  12 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.  Sporolide B: Synthetic Studies.

Authors:  Jeffery A Gladding; James P Bacci; Scott A Shaw; Amos B Smith
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

6.  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

Review 7.  Acyclic Twisted Amides.

Authors:  Guangrong Meng; Jin Zhang; Michal Szostak
Journal:  Chem Rev       Date:  2021-08-18       Impact factor: 72.087

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.  (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

10.  Discovery and development of the anticancer agent salinosporamide A (NPI-0052).

Authors:  William Fenical; Paul R Jensen; Michael A Palladino; Kin S Lam; G Kenneth Lloyd; Barbara C Potts
Journal:  Bioorg Med Chem       Date:  2008-11-05       Impact factor: 3.641
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