Literature DB >> 15149210

A simple stereocontrolled synthesis of salinosporamide A.

Leleti Rajender Reddy1, P Saravanan, E J Corey.   

Abstract

A simple and effective stereocontrolled synthesis of salinosporamide A has been developed. This process, the first synthesis of salinosporamide A, is capable of providing the compound in substantial quantities for further biological studies. Salinosporamide A was of special interest as a synthetic target because of its potent in vitro cytotoxic activity against many tumor cell lines (IC(50) values of 10 nM or less).

Entities:  

Mesh：

Substances：

Year:  2004        PMID： 15149210     DOI： 10.1021/ja048613p

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  23 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.  Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters.

Authors:  Edward Miller; Suhong Kim; Katarina Gibson; Jeffrey S Derrick; F Dean Toste
Journal:  J Am Chem Soc       Date:  2020-04-30       Impact factor: 15.419

3.  Nitrenium ion azaspirocyclization-spirodienone cleavage: a new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams.

Authors:  Duncan J Wardrop; Matthew S Burge
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

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.  Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations.

Authors:  Shi Chen; Ahmad A Ibrahim; Nicholas J Peraino; Divya Nalla; Mukulesh Mondal; Maxwell Van Raaphorst; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2016-08-12       Impact factor: 4.354

7.  Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones.

Authors:  Aaron Christopher; Dahniel Brandes; Stephen Kelly; Thomas G Minehan
Journal:  Org Biomol Chem       Date:  2013-10-10       Impact factor: 3.876

8.  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 9.  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

10.  (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
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.