Literature DB >> 21133399

Total synthesis of (+)-condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine.

Connor L Martin1, Seiichi Nakamura, Ralf Otte, Larry E Overman.   

Abstract

The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are reported. (+)-Condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine were prepared in high enantiomeric purity (er > 99:1) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one 7b by way of five or six isolated intermediates.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 21133399      PMCID： PMC3014433          DOI： 10.1021/ol102709s

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


  6 in total

1.  Total synthesis of (+/-)- and (-)-actinophyllic acid.

Authors:  Connor L Martin; Larry E Overman; Jason M Rohde
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

2.  Palladium(0)-Catalyzed Heteroarylation of 2- and 3-Indolylzinc Derivatives. An Efficient General Method for the Preparation of (2-Pyridyl)indoles and Their Application to Indole Alkaloid Synthesis.

Authors:  Mercedes Amat; Sabine Hadida; Grigorii Pshenichnyi; Joan Bosch
Journal:  J Org Chem       Date:  1997-05-16       Impact factor: 4.354

3.  Kopsiyunnanines F and isocondylocarpines: new tubotaiwine-type alkaloids from Yunnan Kopsia arborea.

Authors:  Yuqiu Wu; Mariko Kitajima; Noriyuki Kogure; Yunsong Wang; Rongping Zhang; Hiromitsu Takayama
Journal:  J Nat Med       Date:  2009-04-28       Impact factor: 2.343

4.  A new acyl radical-based route to the 1,5-methanoazocino[4,3-b]indole framework of uleine and Strychnos alkaloids.

Authors:  M-Lluïsa Bennasar; Tomàs Roca; Davinia García-Díaz
Journal:  J Org Chem       Date:  2008-10-17       Impact factor: 4.354

5.  Enantioselective synthesis of (--)-gilbertine via a cationic cascade cyclization.

Authors:  Jan Jiricek; Siegfried Blechert
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419

6.  Total synthesis of (+/-)-actinophyllic acid.

Authors:  Connor L Martin; Larry E Overman; Jason M Rohde
Journal:  J Am Chem Soc       Date:  2008-05-21       Impact factor: 15.419
  6 in total
  3 in total

1.  Concise total synthesis of (±)-actinophyllic acid.

Authors:  Brett A Granger; Ivan T Jewett; Jeffrey D Butler; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

2.  Synthesis of Structurally Diverse 2,3-Fused Indoles via Microwave-Assisted AgSbF6-Catalysed Intramolecular Difunctionalization of o-Alkynylanilines.

Authors:  Yuanqiong Huang; Yan Yang; Hongjian Song; Yuxiu Liu; Qingmin Wang
Journal:  Sci Rep       Date:  2015-08-27       Impact factor: 4.379

Review 3.  Synthesis and stereochemical determination of an antiparasitic pseudo-aminal type monoterpene indole alkaloid.

Authors:  Yoshihiko Noguchi; Tomoyasu Hirose; Aki Ishiyama; Masato Iwatsuki; Kazuhiko Otoguro; Toshiaki Sunazuka; Satoshi Ōmura
Journal:  J Nat Med       Date:  2016-06-21       Impact factor: 2.343
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.