Literature DB >> 26034329

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

Cristian Draghici1, Jon T Njardarson1.   

Abstract

This review summarizes all published total and formal syntheses as well as synthetic approaches towards vinigrol. The content is divided into sections, which are focused on each research groups contributions and how far each approach was advanced towards vinigrol. Graphical summaries of all the published vinigrol structural perspectives, starting materials used for each routes and a discussion of preferred or privileged reactions employed is also presented.

Entities:  

Keywords:  Diels-Alder; diterpenoid; fragmentation; total synthesis; vinigrol

Year:  2015        PMID: 26034329      PMCID: PMC4447714          DOI: 10.1016/j.tet.2015.04.073

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  24 in total

1.  Synthesis of the complete carbocyclic skeleton of vinigrol.

Authors:  Lionel Gentric; Issam Hanna; Louis Ricard
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005

2.  A formal synthesis of vinigrol.

Authors:  Jason Poulin; Christiane M Grisé-Bard; Louis Barriault
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-19       Impact factor: 15.336

3.  A concise approach to vinigrol.

Authors:  Thomas J Maimone; Ana-Florina Voica; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Fragmentation enables complexity in the first total synthesis of vinigrol.

Authors:  Jin-Yong Lu; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-22       Impact factor: 15.336

5.  A domino enyne/IMDA approach to the core structure of (-) vinigrol.

Authors:  Vipul V Betkekar; Ashik A Sayyad; Krishna P Kaliappan
Journal:  Org Lett       Date:  2014-10-13       Impact factor: 6.005

6.  Exploratory studies aimed at a synthesis of vinigrol. 2. Attempts to exploit ring-closing metathesis for construction of the central cyclooctane belt.

Authors:  Leo A Paquette; Ivan Efremov; Zuosheng Liu
Journal:  J Org Chem       Date:  2005-01-21       Impact factor: 4.354

7.  Exploratory studies aimed at a synthesis of vinigrol. 4. Probe of possible means for direct connection of the side arms and of ring-contraction alternatives.

Authors:  Leo A Paquette; Zuosheng Liu; Ivan Efremov
Journal:  J Org Chem       Date:  2005-01-21       Impact factor: 4.354

8.  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

Review 9.  Synthetic studies inspired by vinigrol.

Authors:  Alexander D Huters; Neil K Garg
Journal:  Chemistry       Date:  2010-08-02       Impact factor: 5.236

10.  Convergent enantioselective synthesis of vinigrol, an architecturally novel diterpenoid with potent platelet aggregation inhibitory and antihypertensive properties. 1. Application of anionic sigmatropy to construction of the octalin substructure.

Authors:  Leo A Paquette; Ronan Guevel; Shuichi Sakamoto; In Ho Kim; Jason Crawford
Journal:  J Org Chem       Date:  2003-08-08       Impact factor: 4.354

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