Literature DB >> 19231870

Synthesis of (+)-coronafacic acid.

Douglass F Taber1, Ritesh B Sheth, Weiwei Tian.   

Abstract

An enantioselective synthesis of (+)-coronafacic acid has been achieved. Rhodium-catalyzed cyclization of an alpha-diazoester provided the intermediate cyclopentanone in high enantiomeric purity. Subsequent Fe-mediated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was hydrogenated and carried on to the natural product.

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Year:  2009        PMID： 19231870      PMCID： PMC2662389          DOI： 10.1021/jo802493k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  17 in total

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Authors:  Masahiro Honma; Takashi Sawada; Yuri Fujisawa; Masayuki Utsugi; Hideaki Watanabe; Akinori Umino; Takehiko Matsumura; Takayuki Hagihara; Masashi Takano; Masahisa Nakada
Journal:  J Am Chem Soc       Date:  2003-03-12       Impact factor: 15.419

2.  Efficient construction of the clerodane decalin core by an asymmetric Morita-Baylis-Hillman reaction/Lewis acid promoted annulation strategy.

Authors:  Stacy A Rodgen; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-24       Impact factor: 15.336

3.  An enantioselective organocatalytic oxidative dearomatization strategy.

Authors:  Ngoc T Vo; Robert D M Pace; Fionn O'Hara; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419

4.  High enantiocontrol in the intramolecular cyclopropanation of diazo ketones catalyzed by dirhodium(II) complexes with ortho-metalated aryl phosphine ligands.

Authors:  M Barberis; J Pérez-Prieto; S E Stiriba; P Lahuerta
Journal:  Org Lett       Date:  2001-10-18       Impact factor: 6.005

5.  Synthesis of (+)-sulcatine G.

Authors:  Douglass F Taber; Kevin J Frankowski
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

6.  Total synthesis of (+)-cyanthiwigin U.

Authors:  Matthew W B Pfeiffer; Andrew J Phillips
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

7.  Expanding the scope of C-H amination through catalyst design.

Authors:  Christine G Espino; Kristin Williams Fiori; Mihyong Kim; J Du Bois
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

8.  A three-step route to a tricyclic steroid precursor.

Authors:  Douglass F Taber; Ritesh B Sheth
Journal:  J Org Chem       Date:  2008-09-25       Impact factor: 4.354

9.  Separation of the cyclization and rearrangement processes of lanosterol biosynthesis. Enzymic conversion of 20,21-dehydro-2,3-oxidosqualene to a dehydroprotosterol.

Authors:  E J Corey; K Lin; H Yamamoto
Journal:  J Am Chem Soc       Date:  1969-04-09       Impact factor: 15.419

10.  2,5-Dialkyl cyclohexenones by Fe(CO)5-mediated carbonylation of alkenyl cyclopropanes: functional group compatibility.

Authors:  Douglass F Taber; Pramod V Joshi; Kazuo Kanai
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354
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  4 in total

1.  Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition.

Authors:  Min Zhang; Weiping Tang
Journal:  Org Lett       Date:  2012-07-11       Impact factor: 6.005

2.  Intramolecular [1 + 4 + 1] cycloaddition: establishment of the method.

Authors:  Douglass F Taber; Pengfei Guo; Na Guo
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

3.  Synthesis of 6-substituted 1-oxoindanoyl isoleucine conjugates and modeling studies with the COI1-JAZ co-receptor complex of lima bean.

Authors:  Yoko Nakamura; Christian Paetz; Wolfgang Brandt; Anja David; Martha Rendón-Anaya; Alfredo Herrera-Estrella; Axel Mithöfer; Wilhelm Boland
Journal:  J Chem Ecol       Date:  2014-07-10       Impact factor: 2.626

4.  Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.

Authors:  Jianhua Wang; Stephanie A Blaszczyk; Xiaoxun Li; Weiping Tang
Journal:  Chem Rev       Date:  2020-08-05       Impact factor: 72.087
  4 in total

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