Literature DB >> 21786746

A palladium-catalyzed vinylcyclopropane (3+2) cycloaddition approach to the Melodinus alkaloids.

Alexander F G Goldberg1, Brian M Stoltz.   

Abstract

A palladium-catalyzed (3+2) cycloaddition of a vinylcyclopropane and a β-nitrostyrene is employed to rapidly assemble the cyclopentane core of the Melodinus alkaloids. The ABCD ring system of the natural product family is prepared in six steps from commercially available materials.
© 2011 American Chemical Society

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Year:  2011        PMID： 21786746      PMCID： PMC3155617          DOI： 10.1021/ol2017615

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


  7 in total

1.  Enantioselective total synthesis of the Melodinus alkaloid (+)-meloscine.

Authors:  Philipp Selig; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Total synthesis of (±)-meloscine.

Authors:  Yujiro Hayashi; Fuyuhiko Inagaki; Chisato Mukai
Journal:  Org Lett       Date:  2011-03-07       Impact factor: 6.005

3.  A short total synthesis of (±)-epimeloscine and (±)-meloscine enabled by a cascade radical annulation of a divinylcyclopropane.

Authors:  Hanmo Zhang; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

4.  Palladium-catalyzed diastereo- and enantioselective synthesis of substituted cyclopentanes through a dynamic kinetic asymmetric formal [3+2]-cycloaddition of vinyl cyclopropanes and alkylidene azlactones.

Authors:  Barry M Trost; Patrick J Morris
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-23       Impact factor: 15.336

5.  An apocynaceae-alkaloid of a novel type.

Authors:  K Bernauer; G Englert; W Vetter
Journal:  Experientia       Date:  1965-07-15

6.  Total synthesis of meloscine by a [2+2]-photocycloaddition/ring-expansion route.

Authors:  Philipp Selig; Eberhardt Herdtweck; Thorsten Bach
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

7.  Diastereoselective synthesis of tetrahydrofurans via Palladium(0)-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes and aldehydes.

Authors:  Andrew T Parsons; Matthew J Campbell; Jeffrey S Johnson
Journal:  Org Lett       Date:  2008-05-27       Impact factor: 6.005
  7 in total
  10 in total

1.  Highly functionalized donor-acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids.

Authors:  Alexander F G Goldberg; Robert A Craig; Nicholas R O'Connor; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs.

Authors:  Hanmo Zhang; Kyu Ok Jeon; E Ben Hay; Steven J Geib; Dennis P Curran; Matthew G LaPorte
Journal:  Org Lett       Date:  2013-12-06       Impact factor: 6.005

3.  Polarity inversion of donor-acceptor cyclopropanes: disubstituted δ-lactones via enantioselective iridium catalysis.

Authors:  Joseph Moran; Austin G Smith; Ryan M Carris; Jeffrey S Johnson; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-10-31       Impact factor: 15.419

4.  Synthesis studies on the Melodinus alkaloid meloscine.

Authors:  Ken S Feldman; Joshua F Antoline
Journal:  Tetrahedron       Date:  2013-02-04       Impact factor: 2.457

5.  Lewis acid mediated (3 + 2) cycloadditions of donor-acceptor cyclopropanes with heterocumulenes.

Authors:  Alexander F G Goldberg; Nicholas R O'Connor; Robert A Craig; Brian M Stoltz
Journal:  Org Lett       Date:  2012-10-09       Impact factor: 6.005

6.  "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Authors:  Peng-Hao Chen; Brent A Billett; Tatsuhiro Tsukamoto; Guangbin Dong
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

7.  Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.

Authors:  E Ben Hay; Hanmo Zhang; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2014-12-22       Impact factor: 15.419

8.  Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives.

Authors:  Murugesan Thangamani; Subaramaniam Thangamalar; Kannupal Srinivasan
Journal:  RSC Adv       Date:  2021-04-21       Impact factor: 3.361

9.  Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides.

Authors:  Yan Lin; Qijun Wang; Yang Wu; Chang Wang; Hao Jia; Cheng Zhang; Jiaxing Huang; Hongchao Guo
Journal:  RSC Adv       Date:  2018-12-05       Impact factor: 3.361

10.  Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.

Authors:  Jianhua Wang; Stephanie A Blaszczyk; Xiaoxun Li; Weiping Tang
Journal:  Chem Rev       Date:  2020-08-05       Impact factor: 72.087
  10 in total

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