epiquinamide and glutarimide

epiquinamide has been researched along with glutarimide* in 1 studies

Other Studies

1 other study(ies) available for epiquinamide and glutarimide

Article	Year
A versatile approach for the asymmetric syntheses of (1R,9aR)-epiquinamide and (1R,9aR)-homopumiliotoxin 223G. Organic letters, 2006, Mar-30, Volume: 8, Issue:7 [reaction: see text] Using 5b as a common intermediate, the first asymmetric synthesis of (-)-epiquinamide (4) and a formal asymmetric synthesis of (-)-homopumiliotoxin 223G (2) is described. A key feature of our approach is the flexible introduction of a functionalized C(4) side chain to (S)-3-benzyloxyglutarimide 7 in a regio- and diastereoselective manner. Utilization of a tandem Swern oxidation-Grignard addition strategy efficiently prevented racemization. An unexpected NaN(3)-promoted methanesulfonic acid elimination yielded 17, a reaction which could be useful for the syntheses of 8-dehydrodesmethylpumiliotoxins such as alkaloid 235C (3). Topics: Alkaloids; Catalysis; Indolizines; Molecular Structure; Piperidines; Piperidones; Quinolizines; Stereoisomerism	2006

Article

Year

A versatile approach for the asymmetric syntheses of (1R,9aR)-epiquinamide and (1R,9aR)-homopumiliotoxin 223G.

Organic letters, 2006, Mar-30, Volume: 8, Issue:7

[reaction: see text] Using 5b as a common intermediate, the first asymmetric synthesis of (-)-epiquinamide (4) and a formal asymmetric synthesis of (-)-homopumiliotoxin 223G (2) is described. A key feature of our approach is the flexible introduction of a functionalized C(4) side chain to (S)-3-benzyloxyglutarimide 7 in a regio- and diastereoselective manner. Utilization of a tandem Swern oxidation-Grignard addition strategy efficiently prevented racemization. An unexpected NaN(3)-promoted methanesulfonic acid elimination yielded 17, a reaction which could be useful for the syntheses of 8-dehydrodesmethylpumiliotoxins such as alkaloid 235C (3).

Topics: Alkaloids; Catalysis; Indolizines; Molecular Structure; Piperidines; Piperidones; Quinolizines; Stereoisomerism

2006