Literature DB >> 23829448

Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds.

Charles S Shanahan1, Phong Truong, Savannah M Mason, John S Leszczynski, Michael P Doyle.   

Abstract

Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, δ-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.

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Year:  2013        PMID: 23829448      PMCID: PMC3806194          DOI: 10.1021/ol4015199

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


  19 in total

1.  Highly enantioselective catalytic synthesis of functionalized chiral diazoacetoacetates.

Authors:  Xinfang Xu; Wen-Hao Hu; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-31       Impact factor: 15.336

2.  An efficient methodology to substituted furans via oxidation of functionalized α-diazo-β-ketoacetates.

Authors:  Phong Truong; Xinfang Xu; Michael P Doyle
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

3.  (+)- and (-)-mutisianthol: first total synthesis, absolute configuration, and antitumor activity.

Authors:  Graziela G Bianco; Helena M C Ferraz; Arinice M Costa; Letícia V Costa-Lotufo; Cláudia Pessoa; Manoel O de Moraes; Marcus G Schrems; Andreas Pfaltz; Luiz F Silva
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

4.  New alkaloid from the aerial parts of Codonopsis clematidea.

Authors:  Shunsuke Ishida; Mamoru Okasaka; Freddy Ramos; Yoshiki Kashiwada; Yoshihisa Takaishi; Olimjon K Kodzhimatov; Ozodbek Ashurmetov
Journal:  J Nat Med       Date:  2008-01-11       Impact factor: 2.343

5.  Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: a diastereoselective total synthesis of (+/-)-indatraline.

Authors:  Luiz F Silva; Fernanda A Siqueira; Eliane C Pedrozo; Fabiana Y M Vieira; Antônio C Doriguetto
Journal:  Org Lett       Date:  2007-03-20       Impact factor: 6.005

6.  Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Authors:  Xinfang Xu; Maxim O Ratnikov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

7.  The structure of stenine, a new alkaloid occurring in Stemona tuberosa.

Authors:  S Ueo; H Irie; H Harada
Journal:  Chem Pharm Bull (Tokyo)       Date:  1967-06       Impact factor: 1.645

8.  Catalytic addition methods for the synthesis of functionalized diazoacetoacetates and application to the construction of highly substituted cyclobutanones.

Authors:  Michael P Doyle; Kousik Kundu; Albert E Russell
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

9.  Construction of highly functionalized diazoacetoacetates via catalytic Mukaiyama-Michael reactions.

Authors:  Yu Liu; Yu Zhang; Noel Jee; Michael P Doyle
Journal:  Org Lett       Date:  2008-03-20       Impact factor: 6.005

Review 10.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962

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