Literature DB >> 18007432

Synthesis of highly functionalised enantiopure bicyclo[3.2.1]- octane systems from carvone.

Antonio Abad1, Consuelo Agulló, Ana C Cuñat, Ignacio de Alfonso, Ismael Navarro, Noelia Vera.   

Abstract

The commercially available monoterpene carvone has been efficiently converted into the tricyclo[3.2.1.0(2.7)]octane and bicyclo[3.2.1]octane systems characteristic of some biologically active compounds. The sequence used for this transformation involves as key features an intramolecular Diels-Alder reaction of a 5-vinyl-1,3-cyclohexadiene and a cyclopropane ring opening.

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Year:  2004        PMID： 18007432      PMCID： PMC6147354          DOI： 10.3390/90500287

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


  8 in total

1.  Synthesis of Functionalized Bicyclo[3.2.1]octanes and Their Multiple Uses in Organic Chemistry.

Authors:  Marie-Hélène Filippini; Jean Rodriguez
Journal:  Chem Rev       Date:  1999-01-13       Impact factor: 60.622

Review 2.  Natural sesquiterpenoids.

Authors:  Braulio M Fraga
Journal:  Nat Prod Rep       Date:  2002-10       Impact factor: 13.423

3.  ent-trachyloban-3beta-ol, a new cytotoxic diterpene from Croton zambesicus.

Authors:  S Block; C Stévigny; M-C De Pauw-Gillet; E de Hoffmann; G Llabrès; V Adjakidjé; J Quetin-Leclercq
Journal:  Planta Med       Date:  2002-07       Impact factor: 3.352

4.  3-Aryl-2-carbomethoxybicyclo[3.2.1]oct-2-enes inhibit WIN 35,428 binding potently and selectively at the dopamine transporter.

Authors:  P C Meltzer; P Blundell; H Huang; S Liu; Y F Yong; B K Madras
Journal:  Bioorg Med Chem       Date:  2000-03       Impact factor: 3.641

5.  Bicyclo[3.2.1]octanes: synthesis and inhibition of binding at the dopamine and serotonin transporters.

Authors:  P C Meltzer; P Blundell; Z Chen; Y F Yong; B K Madras
Journal:  Bioorg Med Chem Lett       Date:  1999-03-22       Impact factor: 2.823

6.  2-Carbomethoxy-3-aryl-8-bicyclo[3.2.1]octanes: potent non-nitrogen inhibitors of monoamine transporters.

Authors:  P C Meltzer; P Blundell; Y F Yong; Z Chen; C George; M D Gonzalez; B K Madras
Journal:  J Med Chem       Date:  2000-08-10       Impact factor: 7.446

Review 7.  Diterpenoids.

Authors:  James R Hanson
Journal:  Nat Prod Rep       Date:  2002-04       Impact factor: 13.423

8.  Intramolecular Diels-Alder reactions of 5-vinyl-1,3-cyclohexadienes.

Authors:  Stephanie M Ng; Christopher M Beaudry; Dirk Trauner
Journal:  Org Lett       Date:  2003-05-15       Impact factor: 6.005
  8 in total

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