Literature DB >> 28537406

Total Synthesis of (+)-Pancratistatin by the Rh(III)-Catalyzed Addition of a Densely Functionalized Benzamide to a Sugar-Derived Nitroalkene.

Tyler J Potter1, Jonathan A Ellman1.   

Abstract

Herein, we report the concise total synthesis of (+)-pancratistatin, accessed in a 10-step linear sequence from commercially available inputs. The convergent synthesis features a highly diastereoselective Rh(III)-catalyzed C-H bond addition to a d-glucose-derived nitroalkene and a late-stage intramolecular transamidation to furnish the B ring lactam.

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Year:  2017        PMID： 28537406      PMCID： PMC5541686          DOI： 10.1021/acs.orglett.7b01220

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


  25 in total

Review 1.  Towards mild metal-catalyzed C-H bond activation.

Authors:  Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal:  Chem Soc Rev       Date:  2011-06-10       Impact factor: 54.564

2.  C-H functionalization logic in total synthesis.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  Chem Soc Rev       Date:  2011-02-07       Impact factor: 54.564

3.  β-Silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone for the total synthesis of (±)-pancratistatin.

Authors:  Yong-Geun Jung; Ho-Ung Kang; Hyun-Kyu Cho; Cheon-Gyu Cho
Journal:  Org Lett       Date:  2011-10-10       Impact factor: 6.005

4.  Pancratistatin selectively targets cancer cell mitochondria and reduces growth of human colon tumor xenografts.

Authors:  Carly Griffin; Aditya Karnik; James McNulty; Siyaram Pandey
Journal:  Mol Cancer Ther       Date:  2011-01       Impact factor: 6.261

5.  Pancratistatin induces apoptosis and autophagy in metastatic prostate cancer cells.

Authors:  Carly Griffin; James McNulty; Siyaram Pandey
Journal:  Int J Oncol       Date:  2011-03-17       Impact factor: 5.650

Review 6.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

Review 7.  Application of donor/acceptor-carbenoids to the synthesis of natural products.

Authors:  Huw M L Davies; Justin R Denton
Journal:  Chem Soc Rev       Date:  2009-09-30       Impact factor: 54.564

8.  Amaryllidaceae isocarbostyril alkaloids and their derivatives as promising antitumor agents.

Authors:  Laurent Ingrassia; Florence Lefranc; Véronique Mathieu; Francis Darro; Robert Kiss
Journal:  Transl Oncol       Date:  2008-03       Impact factor: 4.243

9.  (E)-β-borylstyrene in the Diels-Alder reaction with 3,5-dibromo-2-pyrone for the syntheses of (±)-1-epi-pancratistatin and (±)- pancratistatin.

Authors:  Hyun-Kyu Cho; Hwa-Yeon Lim; Cheon-Gyu Cho
Journal:  Org Lett       Date:  2013-10-28       Impact factor: 6.005

10.  Enantioselective synthesis of protected nitrocyclohexitols with five stereocenters. Total synthesis of (+)-pancratistatin.

Authors:  Fernando Cagide-Fagín; Olaia Nieto-García; Hugo Lago-Santomé; Ricardo Alonso
Journal:  J Org Chem       Date:  2012-12-03       Impact factor: 4.354
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  4 in total

1.  Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.

Authors:  Tanner W Bingham; Lucas W Hernandez; Daniel G Olson; Riley L Svec; Paul J Hergenrother; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

2.  Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.

Authors:  Lucas W Hernandez; Jola Pospech; Ulrich Klöckner; Tanner W Bingham; David Sarlah
Journal:  J Am Chem Soc       Date:  2017-10-25       Impact factor: 15.419

3.  RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones via Annulation of N-Methoxyamides and Nitroalkenes.

Authors:  Tyler J Potter; Yuantao Li; Michael D Ward; Jonathan A Ellman
Journal:  European J Org Chem       Date:  2018-06-11

4.  Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

Authors:  Yuxiang Zhao; Yanren Zhu; Guolan Ma; Qi Wei; Shaoxiong Yang; Xiaoyu Zeng; Hongbin Zhang; Jingbo Chen
Journal:  Chem Sci       Date:  2021-06-21       Impact factor: 9.825
  4 in total

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