Literature DB >> 18259147

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

Luis Espinoza Catalán1, Karen Catalán Marín, Héctor Carrasco Altamirano, Mauricio Cuellar Fritis, María Cristina Chamy.   

Abstract

A route for the degradation of the side chain of ent-labdane derivatives has been devised, giving the useful synthon 2beta,12-dihydroxy-13,14,15,16,17-pentanor-ent-labdane-8-one (8). The use of this compound in the preparation of terpenylquinone derivatives shall be reported elsewhere. In addition we have synthesized the compound 2beta,12-diacetoxy-8beta,17-epoxy-13,14,15,16-tetranor-ent-labdane (10), which upon catalytic epoxide ring opening in alkaline or acid media gave rise in all cases to the formation of tricyclicc ompounds.

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Year:  2007        PMID： 18259147      PMCID： PMC6149105          DOI： 10.3390/12122605

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  8 in total

1.  Activity of drimane antifeedants and related compounds against aphids, and comparative biological effects and chemical reactivity of (-)- and (+)-polygodial.

Authors:  Y Asakawa; G W Dawson; D C Griffiths; J Y Lallemand; S V Ley; K Mori; A Mudd; M Pezechk-Leclaire; J A Pickett; H Watanabe; C M Woodcock; Z Zhong-Ning
Journal:  J Chem Ecol       Date:  1988-10       Impact factor: 2.626

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

Authors:  E J Alvarez-Manzaneda; R Chahboun; I Barranco Pérez; E Cabrera; E Alvarez; R Alvarez-Manzaneda
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

3.  Oxidation of -ketoacyl derivatives. Rearrangement of pyruvates to malonates.

Authors:  M L Rueppel; H Rapoport
Journal:  J Am Chem Soc       Date:  1972-05-31       Impact factor: 15.419

4.  New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.

Authors:  J M Miguel Del Corral; M Gordaliza; M A Castro; M M Mahiques; P Chamorro; A Molinari; M D García-Grávalos; H B Broughton; A San Feliciano
Journal:  J Med Chem       Date:  2001-04-12       Impact factor: 7.446

5.  Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds.

Authors:  A F Barrero; E J Alvarez-Manzaneda; M M Herrador; R Chahboun; P Galera
Journal:  Bioorg Med Chem Lett       Date:  1999-08-16       Impact factor: 2.823

6.  Enantiospecific synthesis of the antituberculosis marine sponge metabolite (+)-puupehenone. The arenol oxidative activation route.

Authors:  Stéphane Quideau; Marjolaine Lebon; Anne-Marie Lamidey
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

7.  Oxidative degradations of the side chain of unsaturated ent-labdanes. Part I.

Authors:  Luis Espinoza Catalán; Héctor Carrasco Altamirano; Mauricio Cuellar Fritis; Claudio Gallardo Araya; Karen Catalán Marín
Journal:  Molecules       Date:  2007-03-06       Impact factor: 4.411

8.  Comparison of the antimicrobial and cytotoxic activities of twenty unsaturated sesquiterpene dialdehydes from plants and mushrooms.

Authors:  H Anke; O Sterner
Journal:  Planta Med       Date:  1991-08       Impact factor: 3.352
  8 in total
  1 in total

1.  Diterpenylhydroquinones from natural ent-labdanes induce apoptosis through decreased mitochondrial membrane potential.

Authors:  Joan Villena; Alejandro Madrid; Iván Montenegro; Enrique Werner; Mauricio Cuellar; Luis Espinoza
Journal:  Molecules       Date:  2013-05-10       Impact factor: 4.411
  1 in total

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