Literature DB >> 17523674

Expedient syntheses of antofine and cryptopleurine via intramolecular 1,3-dipolar cycloaddition.

Sanghee Kim1, Yun Mi Lee, Jaekwang Lee, Taeho Lee, Ye Fu, Yanling Song, Jihee Cho, Deukjoon Kim.   

Abstract

The practical and expedient total syntheses of the representative phenanthroindolizidine and phenanthroquinolizidine alkaloids, antofine and cryptopleurine, are described. Construction of the pyrrolidine and piperidine ring of each alkaloid was achieved by using an intramolecular 1,3-dipolar cycloaddition of an azide onto an alkene and subsequent reduction of the resulting imine and aziridine.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17523674     DOI： 10.1021/jo070668x

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


  7 in total

1.  Total synthesis of (+)-antofine and (-)-cryptopleurine.

Authors:  Weijiang Ying; James W Herndon
Journal:  European J Org Chem       Date:  2013-05-01

2.  Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Authors:  Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

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

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

4.  Antitumor agents 268. Design, synthesis, and mechanistic studies of new 9-substituted phenanthrene-based tylophorine analogues as potent cytotoxic agents.

Authors:  Xiaoming Yang; Qian Shi; Yi-Nan Liu; Guiyu Zhao; Kenneth F Bastow; Jau-Chen Lin; Shuenn-Chen Yang; Pan-Chyr Yang; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2009-08-27       Impact factor: 7.446

5.  Direct synthesis of arenecarboxamides through Friedel-Crafts acylation using ureas.

Authors:  Wenjiang Ying; Lalith S R Gamage; Luke R Lovro; James W Herndon; Nathan W Jenkins; James W Herndon
Journal:  Tetrahedron Lett       Date:  2014-08-13       Impact factor: 2.415

6.  Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles.

Authors:  Pavol Jakubec; Dane M Cockfield; Madeleine Helliwell; James Raftery; Darren J Dixon
Journal:  Beilstein J Org Chem       Date:  2012-04-16       Impact factor: 2.883

7.  Derivatives of salarin A, salarin C and tulearin A--Fascaplysinopsis sp. metabolites.

Authors:  Lee Goren Zur; Ashgan Bishara; Maurice Aknin; Drorit Neumann; Nathalie Ben-Califa; Yoel Kashman
Journal:  Mar Drugs       Date:  2013-11-11       Impact factor: 5.118
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.