Literature DB >> 16774281

Ga(III)-catalyzed cycloisomerization strategy for the synthesis of icetexane diterpenoids: total synthesis of (+/-)-salviasperanol.

Eric M Simmons1, Richmond Sarpong.   

Abstract

[reaction: see text] A general approach to the tricyclic core of the icetexane natural products via the cycloisomerization of alkynyl indenes using GaCl(3) is presented. This strategy provides an efficient synthesis of the natural product salviasperanol and sets the stage for access to other members of this family of diterpenoids.

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Year:  2006        PMID: 16774281     DOI: 10.1021/ol061037c

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


  9 in total

1.  Remarkable facilitation of hetero-cycloisomerizations with water and other polar protic solvents: metal-free synthesis of indolizines.

Authors:  Alison R Hardin Narayan; Richmond Sarpong
Journal:  Green Chem       Date:  2010       Impact factor: 10.182

2.  Ga(III)-catalyzed cycloisomerization approach to (+/-)-icetexone and (+/-)-epi-icetexone.

Authors:  Felipe de Jesus Cortez; Richmond Sarpong
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

3.  Gallium(III)-catalyzed cycloisomerization approach to the diterpenoid alkaloids: construction of the core structure for the hetidines and hetisines.

Authors:  Amy M Hamlin; Felipe de Jesus Cortez; David Lapointe; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-26       Impact factor: 15.336

4.  A Rh(II)-catalyzed cycloaddition approach towards the synthesis of komaroviquinone.

Authors:  Albert Padwa; Majid J Chughtai; Jutatip Boonsombat; Paitoon Rashatasakhon
Journal:  Tetrahedron       Date:  2008-05-19       Impact factor: 2.457

5.  Synthetic studies on the icetexones: enantioselective formal syntheses of icetexone and epi-icetexone.

Authors:  Felipe de Jesus Cortez; David Lapointe; Amy M Hamlin; Eric M Simmons; Richmond Sarpong
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

6.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

7.  Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.

Authors:  Zhi-Wei Jiao; Yong-Qiang Tu; Qing Zhang; Wen-Xing Liu; Shu-Yu Zhang; Shao-Hua Wang; Fu-Min Zhang; Sen Jiang
Journal:  Nat Commun       Date:  2015-06-17       Impact factor: 14.919

8.  Studies on C20-diterpenoid alkaloids: synthesis of the hetidine framework and its application to the synthesis of dihydronavirine and the atisine skeleton.

Authors:  Amy M Hamlin; David Lapointe; Kyle Owens; Richmond Sarpong
Journal:  J Org Chem       Date:  2014-07-11       Impact factor: 4.354

9.  Structure, Absolute Configuration, and Antiproliferative Activity of Abietane and Icetexane Diterpenoids from Salvia ballotiflora.

Authors:  Baldomero Esquivel; Celia Bustos-Brito; Mariano Sánchez-Castellanos; Antonio Nieto-Camacho; Teresa Ramírez-Apan; Pedro Joseph-Nathan; Leovigildo Quijano
Journal:  Molecules       Date:  2017-10-18       Impact factor: 4.411

  9 in total

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