Literature DB >> 21671591

Total synthesis of (±)-trigonoliimine C via oxidative rearrangement of an unsymmetrical bis-tryptamine.

Xiangbing Qi1, Hongli Bao, Uttam K Tambar.   

Abstract

We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2'-bis-tryptamine.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21671591     DOI： 10.1021/ja203960b

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


  7 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.

Authors:  Sunkyu Han; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-10-31       Impact factor: 4.354

3.  Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Evan D Styduhar; Alexander D Huters; Nicholas A Weires; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

4.  Electrophilic Oxidation and [1,2]-Rearrangement of the Biindole Core of Birinapant.

Authors:  Yijun Deng; Thomas Haimowitz; Matthew G LaPorte; Susan R Rippin; Matthew D Alexander; Pavan Tirunahari Kumar; Mukta S Hendi; Yu-Hua Lee; Stephen M Condon
Journal:  ACS Med Chem Lett       Date:  2016-01-09       Impact factor: 4.345

5.  Palladium-catalyzed direct C(sp3)-H arylation of indole-3-ones with aryl halides: a novel and efficient method for the synthesis of nucleophilic 2-monoarylated indole-3-ones.

Authors:  Yong-Long Zhao; Yong-Qin Tang; Xing-Hai Fei; Tao Xiao; Ya-Dong Lu; Xiao-Zhong Fu; Bin He; Meng Zhou; Chun Li; Peng-Fei Xu; Yuan-Yong Yang
Journal:  RSC Adv       Date:  2018-07-16       Impact factor: 3.361

6.  Advances in the chemistry of oxaziridines.

Authors:  Kevin S Williamson; David J Michaelis; Tehshik P Yoon
Journal:  Chem Rev       Date:  2014-04-22       Impact factor: 60.622

7.  Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.

Authors:  Xin Zhang; Richard J Staples; Arnold L Rheingold; William D Wulff
Journal:  J Am Chem Soc       Date:  2014-09-23       Impact factor: 15.419
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.