Literature DB >> 30887693

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

Hadi Gholami1, Aman Kulshrestha1, Olivia K Favor1, Richard J Staples1, Babak Borhan1.   

Abstract

The synthesis of (-)-salinosporamide A, a proteasome inhibitor, is described. The synthesis highlights the assembly of a densely decorated pyrrolidinone core via an aza-Payne/hydroamination sequence. Central to the success of the synthesis is a late-stage C-H insertion reaction to functionalize a sterically encumbered secondary carbon. The latter functionalization leads to an enabling transformation where most of the prototypical strategies failed.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H insertion; aza-Payne reactions; hydroamination; salinosporamide A; total synthesis

Year:  2019        PMID： 30887693      PMCID： PMC6715302          DOI： 10.1002/anie.201900340

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  38 in total

1.  Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora.

Authors:  Robert H Feling; Greg O Buchanan; Tracy J Mincer; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-20       Impact factor: 15.336

2.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.

Authors:  Huw M L Davies; Rohan E J Beckwith
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

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

Authors:  Leleti Rajender Reddy; Jean-François Fournier; B V Subba Reddy; E J Corey
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

4.  An efficient, stereocontrolled synthesis of a potent omuralide-salinosporin hybrid for selective proteasome inhibition.

Authors:  Leleti Rajender Reddy; Jean-François Fournier; B V Subba Reddy; E J Corey
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

5.  A stereoselective synthesis of (-)-tetrodotoxin.

Authors:  Andrew Hinman; J Du Bois
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

6.  Total synthesis of (-)-kaitocephalin.

Authors:  Masanori Kawasaki; Tetsuro Shinada; Makoto Hamada; Yasufumi Ohfune
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

7.  Total synthesis of salinosporamide A.

Authors:  Atsushi Endo; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

8.  Selective 1,5-alkylidenecarbene insertion reactions on [3.2.1] oxabicyclic ethers: a new approach toward the AB ring system of ingenol.

Authors:  Richard S Grainger; Richard B Owoare
Journal:  Org Lett       Date:  2004-08-19       Impact factor: 6.005

9.  Alkylidenecarbenes, alkylidenecarbenoids, and competing species: which is responsible for vinylic nucleophilic substitution, [1 + 2] cycloadditions, 1,5-CH insertions, and the Fritsch-Buttenberg-Wiechell rearrangement?

Authors:  Rudolf Knorr
Journal:  Chem Rev       Date:  2004-09       Impact factor: 60.622

10.  A simple stereocontrolled synthesis of salinosporamide A.

Authors:  Leleti Rajender Reddy; P Saravanan; E J Corey
Journal:  J Am Chem Soc       Date:  2004-05-26       Impact factor: 15.419
View more
  3 in total

Review 1.  Highlights of marine natural products having parallel scaffolds found from marine-derived bacteria, sponges, and tunicates.

Authors:  Erin P McCauley; Ivett C Piña; Alyssa D Thompson; Kashif Bashir; Miriam Weinberg; Shannon L Kurz; Phillip Crews
Journal:  J Antibiot (Tokyo)       Date:  2020-06-08       Impact factor: 2.649

2.  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

3.  Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols.

Authors:  Claire Empel; Chao Pei; Feifei He; Sripati Jana; Rene M Koenigs
Journal:  Chemistry       Date:  2022-02-17       Impact factor: 5.020
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.