Literature DB >> 17362025

Synthesis of the tricyclic core of vinigrol via an intramolecular Diels-Alder reaction.

Christiane M Grisé1, Guillaume Tessier, Louis Barriault.   

Abstract

[reaction: see text] Herein, we present a successful synthesis of the tricyclic core of vinigrol (1). Our approach takes advantage of a highly regioselective intramolecular Diels-Alder reaction of the diene 11 to construct two rings of the tricyclic vinigrol skeleton 12.

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Year:  2007        PMID： 17362025     DOI： 10.1021/ol0702977

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


  6 in total

1.  Total synthesis of vinigrol.

Authors:  Thomas J Maimone; Jun Shi; Shinji Ashida; Phil S Baran
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

2.  Synthetic Approaches and Total Syntheses of Vinigrol, a Unique Diterpenoid.

Authors:  Cristian Draghici; Jon T Njardarson
Journal:  Tetrahedron       Date:  2015-06-10       Impact factor: 2.457

3.  Evolution of an oxidative dearomatization enabled total synthesis of vinigrol.

Authors:  Qingliang Yang; Cristian Draghici; Jon T Njardarson; Fang Li; Brandon R Smith; Pradipta Das
Journal:  Org Biomol Chem       Date:  2014-01-14       Impact factor: 3.876

4.  Why a proximity-induced Diels-Alder reaction is so fast.

Authors:  Elizabeth H Krenske; Emma W Perry; Steven V Jerome; Thomas J Maimone; Phil S Baran; K N Houk
Journal:  Org Lett       Date:  2012-05-25       Impact factor: 6.005

5.  Total synthesis of vinigrol.

Authors:  Qingliang Yang; Jon T Njardarson; Cristian Draghici; Fang Li
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-01       Impact factor: 15.336

6.  Rapid assembly of vinigrol's unique carbocyclic skeleton.

Authors:  Jason G M Morton; Cristian Draghici; Laura D Kwon; Jon T Njardarson
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005
  6 in total

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