Literature DB >> 12188646

Asymmetric total synthesis of dendrobatid alkaloid 251F.

Aaron Wrobleski1, Kiran Sahasrabudhe, Jeffrey Aubé.   

Abstract

The dendrobatid alkaloid (-)-251F was synthesized. The key steps of the synthesis were (1) an asymmetric Diels-Alder reaction to establish four of the necessary stereocenters in the target, (2) a ring-opening/ring-closing metathesis reaction to establish a key [3.3.0] bicyclic intermediate, and (3) an intramolecular Schmidt reaction.

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Year:  2002        PMID: 12188646     DOI: 10.1021/ja027113y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Total synthesis of aburatubolactam A.

Authors:  James A Henderson; Andrew J Phillips
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.

Authors:  Ruzhang Liu; Osvaldo Gutierrez; Dean J Tantillo; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2012-04-10       Impact factor: 15.419

3.  Stereoselective phosphine-catalyzed synthesis of highly functionalized diquinanes.

Authors:  Jonathan E Wilson; Jianwei Sun; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

4.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

5.  Catalytic asymmetric synthesis using feedstocks: an enantioselective route to 2-arylpropionic acids and 1-arylethyl amines via hydrovinylation of vinyl arenes.

Authors:  Craig R Smith; T V RajanBabu
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

6.  Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds.

Authors:  Wolfgang Maison; Marina Büchert; Nina Deppermann
Journal:  Beilstein J Org Chem       Date:  2007-12-18       Impact factor: 2.883

Review 7.  Recent applications of ring-rearrangement metathesis in organic synthesis.

Authors:  Sambasivarao Kotha; Milind Meshram; Priti Khedkar; Shaibal Banerjee; Deepak Deodhar
Journal:  Beilstein J Org Chem       Date:  2015-10-07       Impact factor: 2.883

  7 in total

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