Literature DB >> 17330147

Lewis acid-promoted alpha-hydroxy beta-dicarbonyl to alpha-ketol ester rearrangement.

Xuechuan Hong1, José M Mejía-Oneto, Albert Padwa.   

Abstract

The decarbomethoxylation reaction of a substituted alpha-hydroxy-alpha-carbomethoxy pentacyclic substituted ketone, used as an advanced intermediate in the synthesis of the alkaloid aspidophytine, can be elected by heating with MgI(2) in CH(3)CN. The reaction was shown to proceed by a novel alpha-hydroxy beta-dicarbonyl to alpha-ketol ester rearrangement. It was possible to isolate a carbonate intermediate in 75% yield, thereby providing support for the proposed pathway.

Entities:  

Year:  2006        PMID： 17330147      PMCID： PMC1805679          DOI： 10.1016/j.tetlet.2006.09.071

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  7 in total

1.  Cascade Processes of Metallo Carbenoids.

Authors:  Albert Padwa; M. David Weingarten
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

Authors:  José M Mejía-Oneto; Albert Padwa
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

3.  Concise, stereoselective syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid via tandem carbonyl ylide formation-cycloaddition.

Authors:  David M Hodgson; Thomas D Avery; Andrew C Donohue
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

4.  The decarbethoxylation of geminal dicarbethoxy compounds.

Authors:  A P Krapcho; G A Glynn; B J Grenon
Journal:  Tetrahedron Lett       Date:  1967-01       Impact factor: 2.415

5.  Utilization of the Intramolecular Cycloaddition-Cationic pi-Cyclization of an Isomünchnone Derivative for the Synthesis of (+/-)-Lycopodine.

Authors:  Albert Padwa; Michael A. Brodney; Joseph P. Marino; Scott M. Sheehan
Journal:  J Org Chem       Date:  1997-01-10       Impact factor: 4.354

6.  Synthesis of (-)-tetracycline.

Authors:  Mark G Charest; Dionicio R Siegel; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

7.  A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids.

Authors:  Bin Chen; Rebecca Y Y Ko; Mabel S M Yuen; Kin-Fai Cheng; Pauline Chiu
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354
  7 in total
  2 in total

1.  Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade.

Authors:  Dylan B England; Albert Padwa
Journal:  Org Lett       Date:  2007-07-21       Impact factor: 6.005

2.  A carbonate-forming Baeyer-Villiger monooxygenase.

Authors:  Youcai Hu; David Dietrich; Wei Xu; Ashay Patel; Justin A J Thuss; Jingjing Wang; Wen-Bing Yin; Kangjian Qiao; K N Houk; John C Vederas; Yi Tang
Journal:  Nat Chem Biol       Date:  2014-05-18       Impact factor: 15.040
  2 in total

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