Literature DB >> 20387896

Synthesis of (+)-complanadine A, an inducer of neurotrophic factor excretion.

Changxia Yuan1, Chih-Tsung Chang, Abram Axelrod, Dionicio Siegel.   

Abstract

A total synthesis of the Lycopodium alkaloid (+)-complanadine A is described. Complanadine A has been shown to induce the secretion of neurotrophic factors from 1321N1 cells, promoting the differentiation of PC-12 cells. The use of a simplifying metal mediated [2+2+2] + [2+2+2] sequence using a silyl-substituted diyne and 2 equiv of the corresponding alkyne-nitrile has provided rapid access to the natural product.

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Year:  2010        PMID: 20387896     DOI: 10.1021/ja101956x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  16 in total

1.  A serendipitous discovery: nickel catalyst for the cycloaddition of diynes with unactivated nitriles.

Authors:  Puneet Kumar; Simon Prescher; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-20       Impact factor: 15.336

2.  Organic chemistry: Symmetrizing the unsymmetrical.

Authors:  Scott A Snyder
Journal:  Nature       Date:  2010-06-03       Impact factor: 49.962

Review 3.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

4.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

5.  Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

Authors:  Julie A Pigza; Jeong-Seok Han; Aroop Chandra; Daniel Mutnick; Maren Pink; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

Review 6.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

7.  Development of an enantioselective route toward the Lycopodium alkaloids: total synthesis of lycopodine.

Authors:  Hua Yang; Rich G Carter
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

8.  Enantioselective synthesis of angularly substituted 1-azabicylic rings: coupled dynamic kinetic epimerization and chirality transfer.

Authors:  Zachary D Aron; Tatsuya Ito; Tricia L May; Larry E Overman; Jocelyn Wang
Journal:  J Org Chem       Date:  2013-09-10       Impact factor: 4.354

9.  Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; William C Mobley; Emmanuel A Theodorakis
Journal:  Chemistry       Date:  2013-03-22       Impact factor: 5.236

10.  Synthetic studies on pseudo-dimeric Lycopodium alkaloids: total synthesis of complanadine B.

Authors:  James N Newton; Daniel F Fischer; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-10       Impact factor: 15.336

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