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Literature DB >> 20625460

Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.

Abstract

Disubstituted alpha-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to alpha-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The alpha-hydroxy acid products can be converted into gamma-lactones using a variety of lactonization conditions.

Entities: Chemical Gene

Year: 2009 PMID： 20625460 PMCID： PMC2898151 DOI： 10.1016/j.tet.2009.05.066

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

14 in total

1. Formal total synthesis of (+)-zaragozic acid C through an Ireland-Claisen rearrangement.

Authors: Jens O Bunte; Anthony N Cuzzupe; Alica M Daly; Mark A Rizzacasa
Journal: Angew Chem Int Ed Engl Date: 2006-09-25 Impact factor: 15.336

2. Total synthesis of thapsigargin, a potent SERCA pump inhibitor.

Authors: Matthew Ball; Stephen P Andrews; Frank Wierschem; Ed Cleator; Martin D Smith; Steven V Ley
Journal: Org Lett Date: 2007-01-27 Impact factor: 6.005

3. Silylene transfer to carbonyl compounds and subsequent Ireland-Claisen rearrangements to control formation of quaternary carbon stereocenters.

Authors: Stacie A Calad; K A Woerpel
Journal: J Am Chem Soc Date: 2005-02-23 Impact factor: 15.419

4. A simple, short, and flexible synthesis of viridiofungin derivatives.

Authors: Stephen M Goldup; Christopher J Pilkington; Andrew J P White; Andrew Burton; Anthony G M Barrett
Journal: J Org Chem Date: 2006-08-04 Impact factor: 4.354

5. Dynamic kinetic resolution via dual-function catalysis of modified cinchona alkaloids: asymmetric synthesis of alpha-hydroxy carboxylic acids.

Authors: Liang Tang; Li Deng
Journal: J Am Chem Soc Date: 2002-03-27 Impact factor: 15.419

6. Diastereoselective alkylations of oxazolidinone glycolates: a useful extension of the Evans asymmetric alkylation.

Authors: M T Crimmins; K A Emmitte; J D Katz
Journal: Org Lett Date: 2000-07-13 Impact factor: 6.005

7. Stereoselective preparation of ceramide and its skeleton backbone modified analogues via cyclic thionocarbonate intermediates derived by catalytic asymmetric dihydroxylation of alpha,beta-unsaturated ester precursors.

Authors: L He; H S Byun; R Bittman
Journal: J Org Chem Date: 2000-11-03 Impact factor: 4.354

Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.

1. Formal total synthesis of (+)-zaragozic acid C through an Ireland-Claisen rearrangement.

2. Total synthesis of thapsigargin, a potent SERCA pump inhibitor.

3. Silylene transfer to carbonyl compounds and subsequent Ireland-Claisen rearrangements to control formation of quaternary carbon stereocenters.

4. A simple, short, and flexible synthesis of viridiofungin derivatives.

5. Dynamic kinetic resolution via dual-function catalysis of modified cinchona alkaloids: asymmetric synthesis of alpha-hydroxy carboxylic acids.

6. Diastereoselective alkylations of oxazolidinone glycolates: a useful extension of the Evans asymmetric alkylation.

7. Stereoselective preparation of ceramide and its skeleton backbone modified analogues via cyclic thionocarbonate intermediates derived by catalytic asymmetric dihydroxylation of alpha,beta-unsaturated ester precursors.

8. Synthesis of tertiary alpha-hydroxy acids by silylene transfer to alpha-keto esters.

9. Mechanism of silver-mediated di-tert-butylsilylene transfer from a silacyclopropane to an alkene.

10. Stereoselective iodocyclization of (S)-allylalanine derivatives: gamma-lactone vs cyclic carbamate formation.

1. Synthesis of gamma,delta-unsaturated glycolic acids via sequenced brook and Ireland--claisen rearrangements.

2. Formation of macrocyclic lactones in the Paternò-Büchi dimerization reaction.