Literature DB >> 19728692

Rapid assembly of vinigrol's unique carbocyclic skeleton.

Jason G M Morton1, Cristian Draghici, Laura D Kwon, Jon T Njardarson.   

Abstract

Detailed in this account are our efforts toward the total synthesis of vinigrol. A highly expedient and convergent synthetic approach made possible by the use of a strategic oxidative dearomatization reaction coupled with a series of ensuing substrate controlled transformations is discussed.

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Year:  2009        PMID： 19728692      PMCID： PMC2759413          DOI： 10.1021/ol901519k

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


  15 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.  Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Authors:  D Magdziak; S J Meek; T R R Pettus
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

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

Authors:  Christiane M Grisé; Guillaume Tessier; Louis Barriault
Journal:  Org Lett       Date:  2007-03-16       Impact factor: 6.005

4.  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

5.  Exploratory studies aimed at a synthesis of vinigrol. 3. Evaluation of a lactone bridge as a conformational lock.

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

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.  Intramolecular conjugate addition of alkenyl and aryl functions to enones initiated by lithium-iodine exchange.

Authors:  E Piers; C L Harrison; C Zetina-Rocha
Journal:  Org Lett       Date:  2001-10-18       Impact factor: 6.005

9.  Prevention of undesirable isomerization during olefin metathesis.

Authors:  Soon Hyeok Hong; Daniel P Sanders; Choon Woo Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

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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  8 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.  Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group.

Authors:  Qingliang Yang; Jon T Njardarson
Journal:  Tetrahedron Lett       Date:  2013-12-18       Impact factor: 2.415

4.  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

5.  Syntheses and structural confirmations of members of a heterocycle-containing family of labdane diterpenoids.

Authors:  Daniel J Mack; Jon T Njardarson
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-17       Impact factor: 15.336

6.  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

7.  Formation of Fused Aromatic Architectures via an Oxidative Dearomatization - Radical Cyclization Rearomatization Approach.

Authors:  Edon Vitaku; Jon T Njardarson
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

8.  Unusual Polycyclic Fused Product by Oxidative Enzymatic Dimerisation of 5-methylpyrogallol Catalysed by Horseradish Peroxidase/H₂O₂.

Authors:  Hélène Bouges; Kevin Calabro; Olivier P Thomas; Sylvain Antoniotti
Journal:  Molecules       Date:  2018-10-12       Impact factor: 4.411
  8 in total

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