Literature DB >> 17935340

Synthesis of (+)-vinblastine and its analogues.

Tohru Miyazaki1, Satoshi Yokoshima, Siro Simizu, Hiroyuki Osada, Hidetoshi Tokuyama, Tohru Fukuyama.   

Abstract

A synthetic route to vinblastine and its analogues with an ethynyl group, which features a stereoselective coupling of an 11-membered key intermediate with vindoline, is described. Transformations of the alkynyl moiety including a partial reduction as well as a Sonogashira coupling furnished a variety of analogues.

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Year:  2007        PMID： 17935340     DOI： 10.1021/ol702040y

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


  12 in total

1.  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

2.  10'-Fluorovinblastine and 10'-Fluorovincristine: Synthesis of a Key Series of Modified Vinca Alkaloids.

Authors:  Hiroaki Gotoh; Katharine K Duncan; William M Robertson; Dale L Boger
Journal:  ACS Med Chem Lett       Date:  2011-12-08       Impact factor: 4.345

3.  Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.

Authors:  Annie Tam; Hiroaki Gotoh; William M Robertson; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-09-19       Impact factor: 2.823

4.  Total synthesis and evaluation of a key series of C5-substituted vinblastine derivatives.

Authors:  Porino Va; Erica L Campbell; William M Robertson; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

5.  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

6.  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

7.  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

8.  Total synthesis of Δ¹²-prostaglandin J₃, a highly potent and selective antileukemic agent.

Authors:  K C Nicolaou; Philipp Heretsch; Abdelatif ElMarrouni; Christopher R H Hale; Kiran K Pulukuri; Avinash K Kudva; Vivek Narayan; K Sandeep Prabhu
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-05       Impact factor: 15.336

9.  Potent Vinblastine C20' Ureas Displaying Additionally Improved Activity Against a Vinblastine-Resistant Cancer Cell Line.

Authors:  Timothy J Barker; Katharine K Duncan; Katerina Otrubova; Dale L Boger
Journal:  ACS Med Chem Lett       Date:  2013-09-09       Impact factor: 4.345

Review 10.  Fukuyama reduction, Fukuyama coupling and Fukuyama-Mitsunobu alkylation: recent developments and synthetic applications.

Authors:  Sana Sikandar; Ameer Fawad Zahoor; Shazia Naheed; Bushra Parveen; Kulsoom Ghulam Ali; Rabia Akhtar
Journal:  Mol Divers       Date:  2021-02-11       Impact factor: 2.943
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