Literature DB >> 23391149

Total synthesis of kopsinine.

Jian Xie1, Amanda L Wolfe, Dale L Boger.   

Abstract

The use of a powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of an 1,3,4-oxadiazole in the divergent total synthesis of kopsinine (1), featuring an additional unique SmI(2)-promoted transannular cyclization reaction for formation of the bicyclo[2.2.2]octane central to its hexacyclic ring system, is detailed.

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Year:  2013        PMID： 23391149      PMCID： PMC3578506          DOI： 10.1021/ol303573f

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


  24 in total

1.  Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole.

Authors:  Scott E Wolkenberg; Dale L Boger
Journal:  J Org Chem       Date:  2002-10-18       Impact factor: 4.354

2.  Total synthesis of (-)- and ent-(+)-vindorosine: tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition of 1,3,4-oxadiazoles.

Authors:  Gregory I Elliott; Juraj Velcicky; Hayato Ishikawa; Yongkai Li; Dale L Boger
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-16       Impact factor: 15.336

3.  Total synthesis of (-)-kopsinine by an asymmetric one-pot [n+2+3] cyclization.

Authors:  Shingo Harada; Takeo Sakai; Kiyosei Takasu; Ken-ichi Yamada; Yasutomo Yamamoto; Kiyoshi Tomioka
Journal:  Chem Asian J       Date:  2012-08-21

4.  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

5.  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

6.  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

7.  Synthesis of the Pentacyclic Skeleton of the Aspidosperma Alkaloids Using Rhodium Carbenoids as Reactive Intermediates.

Authors:  Albert Padwa; Alan T. Price
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

8.  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

9.  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

10.  New insights into the mechanism and an expanded scope of the Fe(III)-mediated vinblastine coupling reaction.

Authors:  Hiroaki Gotoh; Justin E Sears; Albert Eschenmoser; Dale L Boger
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419
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  14 in total

1.  Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  Org Lett       Date:  2015-07-14       Impact factor: 6.005

2.  Total synthesis of (-)-kopsinine and ent-(+)-kopsinine.

Authors:  Kiyoun Lee; Dale L Boger
Journal:  Tetrahedron       Date:  2015-06-03       Impact factor: 2.457

3.  Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.

Authors:  Ryan E Quiñones; Christopher M Glinkerman; Kaicheng Zhu; Dale L Boger
Journal:  Org Lett       Date:  2017-06-28       Impact factor: 6.005

Review 4.  Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.

Authors:  Jiajun Zhang; Vyom Shukla; Dale L Boger
Journal:  J Org Chem       Date:  2019-05-23       Impact factor: 4.354

5.  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

6.  Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications.

Authors:  Justin E Sears; Dale L Boger
Journal:  Acc Chem Res       Date:  2016-01-27       Impact factor: 22.384

7.  Transannular Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles: total synthesis of a unique set of vinblastine analogues.

Authors:  Erica L Campbell; Colin K Skepper; Kuppusamy Sankar; Katharine K Duncan; Dale L Boger
Journal:  Org Lett       Date:  2013-10-02       Impact factor: 6.005

8.  Total Synthesis of (-)-Strempeliopine.

Authors:  Xianhuang Zeng; Dale L Boger
Journal:  J Am Chem Soc       Date:  2021-07-29       Impact factor: 16.383

9.  Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation.

Authors:  Kiyoun Lee; Dale L Boger
Journal:  J Am Chem Soc       Date:  2014-02-17       Impact factor: 15.419

10.  Cycloadditions of noncomplementary substituted 1,2,3-triazines.

Authors:  Erin D Anderson; Adam S Duerfeldt; Kaicheng Zhu; Christopher M Glinkerman; Dale L Boger
Journal:  Org Lett       Date:  2014-09-15       Impact factor: 6.005
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