Literature DB >> 26139943

Conformational effects and stereocontrol in synthesis studies of medium-ring dolabellane carbocycles.

David R Williams1, Leslie A Robinson1, Seth A Bawel1.   

Abstract

Stereoselective reactions are described which lead to functionalization of the dolabellane skeleton. The stereoselectivity is attributed to conformational effects imposed by the eleven-membered ring. An efficient pathway provides for the stereocontrolled synthesis of nonracemic 6(S)-hydroxy-4(E)-dolabellene-3-one 12 and related derivatives.

Entities:  

Keywords:  Conformational studies; Dolabellane diterpenes; Medium-ring carbocycles; Stereoselective synthesis

Year:  2015        PMID： 26139943      PMCID： PMC4484730          DOI： 10.1016/j.tetlet.2014.12.049

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  8 in total

1.  Enantioselective total synthesis of (+)- and (-)-nigellamine A2.

Authors:  Jianwei Bian; Matthew Van Wingerden; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

2.  Enantioselective total synthesis of isoedunol and beta-araneosene featuring unconventional strategy and methodology.

Authors:  Jason S Kingsbury; E J Corey
Journal:  J Am Chem Soc       Date:  2005-10-12       Impact factor: 15.419

3.  Concise total syntheses of palominol, dolabellatrienone, beta-araneosene, and isoedunol via an enantioselective Diels-Alder macrobicyclization.

Authors:  Scott A Snyder; E J Corey
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

4.  Strategies for the synthesis of fusicoccanes by Nazarov reactions of dolabelladienones: total synthesis of (+)-fusicoauritone.

Authors:  David R Williams; Leslie A Robinson; C Richard Nevill; Jayachandra P Reddy
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Letter: A novel diterpene from Dollabella californica.

Authors:  C Ireland; D J Faulkner; J Finer; J Clardy
Journal:  J Am Chem Soc       Date:  1976-07-21       Impact factor: 15.419

6.  Dolabellane-type diterpenoids with antiprotozoan activity from a southwestern Caribbean gorgonian octocoral of the genus Eunicea.

Authors:  Xiaomei Wei; Abimael D Rodríguez; Peter Baran; Raphael G Raptis
Journal:  J Nat Prod       Date:  2010-05-28       Impact factor: 4.050

7.  Total synthesis of (+)-4,5-deoxyneodolabelline.

Authors:  David R Williams; Richard W Heidebrecht
Journal:  J Am Chem Soc       Date:  2003-02-19       Impact factor: 15.419

8.  Enantioselective total synthesis of clavirolide C. Applications of Cu-catalyzed asymmetric conjugate additions and Ru-catalyzed ring-closing metathesis.

Authors:  M Kevin Brown; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2008-09-09       Impact factor: 15.419
  8 in total

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