Literature DB >> 11878966

Stereocontrolled total synthesis of (+)-vinblastine.

Satoshi Yokoshima1, Toshihiro Ueda, Satoshi Kobayashi, Ayato Sato, Takeshi Kuboyama, Hidetoshi Tokuyama, Tohru Fukuyama.   

Abstract

A stereocontrolled total synthesis of (+)-vinblastine was accomplished, featuring preparations of the two indole units by means of a novel indole synthesis via radical cyclization of thioanilide, and a stereoselective coupling of these units.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 11878966     DOI： 10.1021/ja0177049

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


  51 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.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

3.  Total synthesis of (-)- and ent-(+)-vindoline.

Authors:  Younggi Choi; Hayato Ishikawa; Juraj Velcicky; Gregory I Elliott; Michael M Miller; Dale L Boger
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

4.  Direct coupling of catharanthine and vindoline to provide vinblastine: total synthesis of (+)- and ent-(-)-vinblastine.

Authors:  Hayato Ishikawa; David A Colby; Dale L Boger
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419

5.  Allenyl azide cycloaddition chemistry. 2,3-cyclopentennelated indole synthesis through indolidene intermediates.

Authors:  Ken S Feldman; D Keith Hester; Malliga R Iyer; Paul J Munson; Carlos Silva López; Olalla Nieto Faza
Journal:  J Org Chem       Date:  2009-07-17       Impact factor: 4.354

6.  Opportunities in metabolic engineering to facilitate scalable alkaloid production.

Authors:  Effendi Leonard; Weerawat Runguphan; Sarah O'Connor; Kristala Jones Prather
Journal:  Nat Chem Biol       Date:  2009-05       Impact factor: 15.040

7.  Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues.

Authors:  Hayato Ishikawa; David A Colby; Shigeki Seto; Porino Va; Annie Tam; Hiroyuki Kakei; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

8.  Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.

Authors:  Kristin D Schleicher; Yoshikazu Sasaki; Annie Tam; Daisuke Kato; Katharine K Duncan; Dale L Boger
Journal:  J Med Chem       Date:  2013-01-04       Impact factor: 7.446

9.  Hypervalent iodine(III)-promoted intermolecular C-C coupling of vindoline with β-ketoesters and related substrates.

Authors:  Travis C Turner; Kotaro Shibayama; Dale L Boger
Journal:  Org Lett       Date:  2013-02-19       Impact factor: 6.005

10.  A remarkable series of vinblastine analogues displaying enhanced activity and an unprecedented tubulin binding steric tolerance: C20' urea derivatives.

Authors:  Erick K Leggans; Katharine K Duncan; Timothy J Barker; Kristin D Schleicher; Dale L Boger
Journal:  J Med Chem       Date:  2012-12-17       Impact factor: 7.446
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.