Literature DB >> 20606761

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

Justin R Struble1, Jeffrey W Bode.   

Abstract

An N-heterocyclic carbene (NHC) catalyzed intramolecular lactonization to prepare densely functionalized bicyclic γ-lactam-γ-lactone adducts from enals is reported. This method has been applied to the formal synthesis of salinosporamide A, a potent 20S proteasome inhibitor and anti-cancer therapeutic.

Entities:  

Year:  2009        PMID： 20606761      PMCID： PMC2896295          DOI： 10.1016/j.tet.2009.03.103

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  28 in total

1.  Chiral N-heterocyclic carbene catalyzed, enantioselective oxodiene Diels-Alder reactions with low catalyst loadings.

Authors:  Ming He; Gerson J Uc; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

2.  Extending mechanistic routes in heterazolium catalysis--promising concepts for versatile synthetic methods.

Authors:  Kirsten Zeitler
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-25       Impact factor: 15.336

3.  Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions.

Authors:  Pei-Chen Chiang; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2007-03-03       Impact factor: 15.419

4.  A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes.

Authors:  Eric M Phillips; Manabu Wadamoto; Audrey Chan; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 5.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

6.  N-heterocyclic carbenes as organocatalysts.

Authors:  Nicolas Marion; Silvia Díez-González; Steven P Nolan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Catalytic Synthesis of gamma-Lactams via direct annulations of enals and N-sulfonylimines.

Authors:  Ming He; Jeffrey W Bode
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

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

Authors:  Taotao Ling; Venkat R Macherla; Rama Rao Manam; Katherine A McArthur; Barbara C M Potts
Journal:  Org Lett       Date:  2007-05-12       Impact factor: 6.005

9.  Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors:  Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

10.  A concise and straightforward total synthesis of (+/-)-salinosporamide A, based on a biosynthesis model.

Authors:  Nicholas P Mulholland; Gerald Pattenden; Iain A S Walters
Journal:  Org Biomol Chem       Date:  2008-05-29       Impact factor: 3.876
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  8 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.  An N-heterocyclic carbene/Lewis acid strategy for the stereoselective synthesis of spirooxindole lactones.

Authors:  Julien Dugal-Tessier; Elizabeth A O'Bryan; Thomas B H Schroeder; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

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

Review 6.  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

Review 7.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

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
  8 in total

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