Literature DB >> 17658832

Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade.

Dylan B England1, Albert Padwa.   

Abstract

A synthesis of (+/-)-3H-epivincamine is reported. Important steps include (1) a Rh(II)-catalyzed intramolecular [3+2]-cycloaddition of an alpha-diazo indolo amide, (2) a reductive ring opening of the cycloadduct, (3) a decarboethoxylation reaction, and (4) a base-induced keto-amide ring contraction.

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Year:  2007        PMID： 17658832      PMCID： PMC2587099          DOI： 10.1021/ol071173x

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


  18 in total

1.  Cascade Processes of Metallo Carbenoids.

Authors:  Albert Padwa; M. David Weingarten
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  A rhodium carbene cyclization-cycloaddition cascade strategy toward the pseudolaric acids.

Authors:  P Chiu; B Chen; K F Cheng
Journal:  Org Lett       Date:  2001-05-31       Impact factor: 6.005

3.  GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS. IV. A SYNTHESIS OF DL-EBURNAMONINE.

Authors:  E WENKERT; B WICKBERG
Journal:  J Am Chem Soc       Date:  1965-04-05       Impact factor: 15.419

4.  A new enantioselective total synthesis of natural vincamine via an intramolecular Mannich reaction of an silyl enol ether.

Authors:  W Oppolzer; H Hauth; P Pfäffli; R Wenger
Journal:  Helv Chim Acta       Date:  1977       Impact factor: 2.164

5.  Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

Authors:  José M Mejía-Oneto; Albert Padwa
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

6.  Cycloaddition chemistry of 2-vinyl-substituted indoles and related heteroaromatic systems.

Authors:  Albert Padwa; Stephen M Lynch; José M Mejía-Oneto; Hongjun Zhang
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

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.  Stereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2,5-dione in carbonyl ylide cycloadditions.

Authors:  David M Hodgson; Frédéric Le Strat; Thomas D Avery; Andrew C Donohue; Tobias Brückl
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

9.  The effects of bromvincamine and vincamine on regional cerebral blood flow and mental functions in patients with multi-infarct dementia.

Authors:  S Hagstadius; L Gustafson; J Risberg
Journal:  Psychopharmacology (Berl)       Date:  1984       Impact factor: 4.530

10.  A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids.

Authors:  Bin Chen; Rebecca Y Y Ko; Mabel S M Yuen; Kin-Fai Cheng; Pauline Chiu
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354
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  1 in total

1.  The Rhodium(II) Carbenoid Cyclization-Cycloaddition Cascade of alpha-Diazo Dihydroindolinones for the Synthesis of Novel Azapolycyclic Ring Systems.

Authors:  Dylan B England; James M Eagan; Gokce Merey; Olcay Anac; Albert Padwa
Journal:  Tetrahedron       Date:  2008-02-04       Impact factor: 2.457
  1 in total

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