Literature DB >> 20704405

Concise total synthesis of (+/-)-pseudotabersonine via double ring-closing metathesis strategy.

Bo Cheng1, James D Sunderhaus, Stephen F Martin.   

Abstract

A concise synthesis of (+/-)-pseudotabersonine from commercially available 1-(phenylsulfonyl)-3-indolecarboxaldehyde has been accomplished. This synthesis features the convergent assembly of a key intermediate via a stepwise variant of a Mannich-type multicomponent coupling process, a double ring-closing metathesis, and a one-pot deprotection/cyclization reaction.

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Year:  2010        PMID： 20704405      PMCID： PMC2921645          DOI： 10.1021/ol101356u

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


  14 in total

1.  Total synthesis of (+)-ambruticin S.

Authors:  T A Kirkland; J Colucci; L S Geraci; M A Marx; M Schneider; D E Kaelin; S F Martin
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2.  Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

Authors:  David G Washburn; Richard W Heidebrecht; Stephen F Martin
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

3.  Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine.

Authors:  Rodrigo B Andrade; Stephen F Martin
Journal:  Org Lett       Date:  2005-12-08       Impact factor: 6.005

4.  Metathesis reactions in total synthesis.

Authors:  K C Nicolaou; Paul G Bulger; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

5.  Synthesis of Diverse Heterocyclic Scaffolds via Tandem Additions to Imine Derivatives and Ring-Forming Reactions.

Authors:  James D Sunderhaus; Chris Dockendorff; Stephen F Martin
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

6.  Total synthesis of indole and dihydroindole alkaloids. I. Introduction and the transannular cyclization appraoch.

Authors:  J P Kutney; E Piers; R T Brown
Journal:  J Am Chem Soc       Date:  1970-03-25       Impact factor: 15.419

7.  Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis.

Authors:  Jason A Deck; Stephen F Martin
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

8.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors:  Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

9.  Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.

Authors:  Christopher E Neipp; Stephen F Martin
Journal:  J Org Chem       Date:  2003-11-14       Impact factor: 4.354

10.  Toward the total synthesis of FR901483: concise synthesis of the azatricyclic skeleton.

Authors:  Suvi T M Simila; Stephen F Martin
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354
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  9 in total

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Journal:  ACS Comb Sci       Date:  2012-02-01       Impact factor: 3.784

2.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

3.  Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives.

Authors:  Simon Hardy; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-10-07       Impact factor: 2.457

4.  Synthesis and biological analysis of truncated calyculone H.

Authors:  Penagaluri Balasubramanyam; Abimael D Rodríguez
Journal:  Tetrahedron       Date:  2017-01-14       Impact factor: 2.457

5.  Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

Authors:  Zhiguo Bian; Christopher C Marvin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

6.  APPLICATIONS OF MULTICOMPONENT ASSEMBLY PROCESSES TO THE FACILE SYNTHESES OF DIVERSELY FUNCTIONALIZED NITROGEN HETEROCYCLES.

Authors:  James R Donald; Brett A Granger; Simon Hardy; James J Sahn; Stephen F Martin
Journal:  Heterocycles       Date:  2011-09-15       Impact factor: 0.831

7.  Facile Syntheses of Substituted, Conformationally-Constrained Benzoxazocines and Benzazocines via Sequential Multicomponent Assembly and Cyclization.

Authors:  James J Sahn; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-12-21       Impact factor: 2.415

8.  Applications of Ring Closing Metathesis. Total Synthesis of (±)-Pseudotabersonine.

Authors:  Bo Cheng; James D Sunderhaus; Stephen F Martin
Journal:  Tetrahedron       Date:  2015-09-30       Impact factor: 2.457

9.  Synthesis of (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine enabled by photoredox catalysis in flow.

Authors:  Joel W Beatty; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2014-07-09       Impact factor: 15.419
  9 in total

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