Literature DB >> 18588345

Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination.

Wei Zeng1, Sherry R Chemler.   

Abstract

The enantioselective synthesis of (S)-(+)-tylophorine, a potent cancer cell growth inhibitor, has been accomplished in eight steps from commercially available 3,4-dimethoxybenzyl alcohol. A copper (II)-catalyzed enantioselective intramolecular alkene carboamination was employed as the key step to construct the chiral indolizidine ring.

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Year:  2008        PMID： 18588345      PMCID： PMC2638068          DOI： 10.1021/jo801024h

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  24 in total

1.  [Stereospecific synthesis of two 9,11,12,13, 13a, 14-hexahydrodibenzo(f,h)pyrrolo(1,2-beta)isoquinolines (author's transl)].

Authors:  L Faber; W Wiegrebe
Journal:  Helv Chim Acta       Date:  1976-09-29       Impact factor: 2.164

2.  The interaction between tylophorine B and TMV RNA.

Authors:  Zhen Xi; Ruoyu Zhang; Zhihong Yu; Di Ouyang
Journal:  Bioorg Med Chem Lett       Date:  2006-06-12       Impact factor: 2.823

3.  Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.

Authors:  Wei Zeng; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

4.  Antitumor agents 251: synthesis, cytotoxic evaluation, and structure-activity relationship studies of phenanthrene-based tylophorine derivatives (PBTs) as a new class of antitumor agents.

Authors:  Linyi Wei; Arnold Brossi; Ross Kendall; Kenneth F Bastow; Susan L Morris-Natschke; Qian Shi; Kuo-Hsiung Lee
Journal:  Bioorg Med Chem       Date:  2006-06-30       Impact factor: 3.641

5.  Synthesis and structure-activity studies of antofine analogues as potential anticancer agents.

Authors:  Ye Fu; Sang Kook Lee; Hye-Young Min; Taeho Lee; Jaekwang Lee; Maosheng Cheng; Sanghee Kim
Journal:  Bioorg Med Chem Lett       Date:  2006-09-30       Impact factor: 2.823

6.  Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C.

Authors:  Alois Fürstner; Jason W J Kennedy
Journal:  Chemistry       Date:  2006-09-25       Impact factor: 5.236

7.  Effect of tylophorine, a major alkaloid of Tylophora indica, on immunopathological and inflammatory reactions.

Authors:  C Gopalakrishnan; D Shankaranarayanan; S K Nazimudeen; L Kameswaran
Journal:  Indian J Med Res       Date:  1980-06       Impact factor: 2.375

8.  Copper(II) acetate promoted oxidative cyclization of arylsulfonyl-o-allylanilines.

Authors:  Eric S Sherman; Sherry R Chemler; Tai Boon Tan; Oksana Gerlits
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

9.  Novel mode of action of tylophorine analogs as antitumor compounds.

Authors:  Wenli Gao; Wing Lam; Sanbao Zhong; Conrad Kaczmarek; David C Baker; Yung-Chi Cheng
Journal:  Cancer Res       Date:  2004-01-15       Impact factor: 12.701

10.  Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism.

Authors:  Eric S Sherman; Peter H Fuller; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Org Chem       Date:  2007-04-12       Impact factor: 4.354
View more
  10 in total

1.  The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

Authors:  Sherry R Chemler
Journal:  Org Biomol Chem       Date:  2009       Impact factor: 3.876

2.  Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.

Authors:  Sherry R Chemler; Shuklendu D Karyakarte; Zainab M Khoder
Journal:  J Org Chem       Date:  2017-09-29       Impact factor: 4.354

3.  Evolution of copper(II) as a new alkene amination promoter and catalyst.

Authors:  Sherry R Chemler
Journal:  J Organomet Chem       Date:  2011-01-01       Impact factor: 2.369

4.  Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues.

Authors:  Xiaoming Yang; Qian Shi; Kenneth F Bastow; Kuo-Hsiung Lee
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

5.  Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidines.

Authors:  Duy N Mai; John P Wolfe
Journal:  J Am Chem Soc       Date:  2010-09-08       Impact factor: 15.419

6.  Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy.

Authors:  Sherry R Chemler
Journal:  Curr Bioact Compd       Date:  2009-03-01

7.  3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

Authors:  Emilia J Groso; Alexander N Golonka; Ryan A Harding; Brandon W Alexander; Taylor M Sodano; Corinna S Schindler
Journal:  ACS Catal       Date:  2018-01-18       Impact factor: 13.084

8.  Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines.

Authors:  Susan Kelleher; Pierre-Yves Quesne; Paul Evans
Journal:  Beilstein J Org Chem       Date:  2009-11-25       Impact factor: 2.883

9.  Enantioselective thiourea-catalyzed intramolecular cope-type hydroamination.

Authors:  Adam R Brown; Christopher Uyeda; Carolyn A Brotherton; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-04-24       Impact factor: 15.419

10.  Identification of phenanthroindolizines and phenanthroquinolizidines as novel potent anti-coronaviral agents for porcine enteropathogenic coronavirus transmissible gastroenteritis virus and human severe acute respiratory syndrome coronavirus.

Authors:  Cheng-Wei Yang; Yue-Zhi Lee; Iou-Jiun Kang; Dale L Barnard; Jia-Tsrong Jan; Du Lin; Chun-Wei Huang; Teng-Kuang Yeh; Yu-Sheng Chao; Shiow-Ju Lee
Journal:  Antiviral Res       Date:  2010-08-19       Impact factor: 5.970
  10 in total

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