Literature DB >> 22369097

Iron(III)/NaBH4-mediated additions to unactivated alkenes: synthesis of novel 20'-vinblastine analogues.

Erick K Leggans1, Timothy J Barker, Katharine K Duncan, Dale L Boger.   

Abstract

An Fe(III)/NaBH(4)-mediated reaction for the functionalization of unactivated alkenes is described defining the alkene substrate scope, establishing the exclusive Markovnikov addition, exploring a range of free radical traps, examining the Fe(III) salt and initiating hydride source, introducing H(2)O-cosolvent mixtures, and exploring catalytic variants. Its use led to the preparation of a novel, potent, and previously inaccessible C20'-vinblastine analogue.

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Year:  2012        PMID： 22369097      PMCID： PMC3306530          DOI： 10.1021/ol300173v

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


  20 in total

1.  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

2.  Mild cobalt-catalyzed hydrocyanation of olefins with tosyl cyanide.

Authors:  Boris Gaspar; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  The discovery of the vinca alkaloids--chemotherapeutic agents against cancer.

Authors:  R L Noble
Journal:  Biochem Cell Biol       Date:  1990-12       Impact factor: 3.626

4.  Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins.

Authors:  Jérôme Waser; Boris Gaspar; Hisanori Nambu; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

5.  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

6.  Asymmetric total synthesis of vindoline.

Authors:  Daisuke Kato; Yoshikazu Sasaki; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

7.  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

8.  Cobalt-catalyzed hydroazidation of olefins: convenient access to alkyl azides.

Authors:  Jérôme Waser; Hisanori Nambu; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

9.  Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues.

Authors:  Yoshikazu Sasaki; Daisuke Kato; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

10.  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
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  71 in total

1.  Synthesis of a Potent Vinblastine: Rationally Designed Added Benign Complexity.

Authors:  Oliver Allemann; Manuela Brutsch; John C Lukesh; Daniel M Brody; Dale L Boger
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

Review 2.  Expanding the enzyme universe: accessing non-natural reactions by mechanism-guided directed evolution.

Authors:  Hans Renata; Z Jane Wang; Frances H Arnold
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-03       Impact factor: 15.336

Review 3.  Natural Products in the "Marketplace": Interfacing Synthesis and Biology.

Authors:  Benjamin J Huffman; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2019-02-13       Impact factor: 15.419

4.  Cycloisomerization of Olefins in Water.

Authors:  Jeishla L M Matos; Samantha A Green; Yuge Chun; Vuong Q Dang; Russell G Dushin; Paul Richardson; Jason S Chen; David W Piotrowski; Brian M Paegel; Ryan A Shenvi
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-28       Impact factor: 15.336

5.  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

6.  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

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.  Divergent Total Syntheses of (-)-Pseudocopsinine and (-)-Minovincinine.

Authors:  Xianhuang Zeng; Vyom Shukla; Dale L Boger
Journal:  J Org Chem       Date:  2020-11-18       Impact factor: 4.354

9.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

10.  Vinblastine 20' Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance.

Authors:  John C Lukesh; Daniel W Carney; Huijun Dong; R Matthew Cross; Vyom Shukla; Katharine K Duncan; Shouliang Yang; Daniel M Brody; Manuela M Brütsch; Aleksandar Radakovic; Dale L Boger
Journal:  J Med Chem       Date:  2017-08-31       Impact factor: 7.446
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