Literature DB >> 15816731

First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol.

E J Alvarez-Manzaneda1, R Chahboun, I Barranco Pérez, E Cabrera, E Alvarez, R Alvarez-Manzaneda.   

Abstract

[reaction: see text] A new route toward puupehenone-related bioactive metabolites from (-)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (-)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyanopuupehenone, were accomplished.

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Year:  2005        PMID: 15816731     DOI: 10.1021/ol047332j

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


  8 in total

1.  Synthetic studies toward (+)-cortistatin A.

Authors:  Zhang Wang; Mingji Dai; Peter K Park; Samuel J Danishefsky
Journal:  Tetrahedron       Date:  2011-10-29       Impact factor: 2.457

2.  A concise synthesis of the cortistatin core.

Authors:  Mingji Dai; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2008-11-17       Impact factor: 2.415

3.  Using enzyme assays to evaluate the structure and bioactivity of sponge-derived meroterpenes.

Authors:  Sarah J Robinson; Eric K Hoobler; Michelle Riener; Steven T Loveridge; Karen Tenney; Frederick A Valeriote; Theodore R Holman; Phillip Crews
Journal:  J Nat Prod       Date:  2009-10       Impact factor: 4.050

4.  Oxidative degradations of the side chain of unsaturated ent-labdanes. Part II.

Authors:  Luis Espinoza Catalán; Karen Catalán Marín; Héctor Carrasco Altamirano; Mauricio Cuellar Fritis; María Cristina Chamy
Journal:  Molecules       Date:  2007-12-21       Impact factor: 4.411

5.  Bispuupehenone from the South Chinese Sea sponge Dysidea sp.

Authors:  Song Qin; Lei Shi; Jia Li; Yue-Wei Guo
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-30

Review 6.  Secondary Metabolites from Polar Organisms.

Authors:  Yuan Tian; Yan-Ling Li; Feng-Chun Zhao
Journal:  Mar Drugs       Date:  2017-02-23       Impact factor: 5.118

Review 7.  Pleiotropic Role of Puupehenones in Biomedical Research.

Authors:  Beatriz Martínez-Poveda; Ana R Quesada; Miguel Ángel Medina
Journal:  Mar Drugs       Date:  2017-10-21       Impact factor: 5.118

8.  Meroxest improves the prognosis of immunocompetent C57BL/6 mice with allografts of E0771 mouse breast tumor cells.

Authors:  Esther Carrasco; Jose Manuel Garrido; Pablo Juan Álvarez; Enrique Álvarez-Manzaneda; Rachid Chahboun; Ibtissam Messouri; Consolación Melguizo; Antonia Aránega; Fernando Rodríguez-Serrano
Journal:  Arch Med Sci       Date:  2016-03-31       Impact factor: 3.318

  8 in total

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