iridoids and carbene

iridoids has been researched along with carbene* in 2 studies

Other Studies

2 other study(ies) available for iridoids and carbene

Article	Year
Concise formal synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters. Organic & biomolecular chemistry, 2011, Dec-07, Volume: 9, Issue:23 NHC catalysed rearrangement of α,β-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated α,β-unsaturated acids provides the cyclopentapyranone core of (-)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps starting from (-)-citronellal. The elaboration to the natural product has been investigated using two new approaches. The most successful intercepts our previous work on (-)-7-deoxyloganin (1) allowing completion of a formal total synthesis in 10-steps. Topics: Catalysis; Esters; Glycosylation; Iridoids; Isomerism; Methane; Molecular Structure; Oxidation-Reduction	2011
The total synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalyzed rearrangement of α,β-unsaturated enol esters. Organic letters, 2010, Nov-05, Volume: 12, Issue:21 The diastereoselective N-heterocyclic carbene (NHC) catalyzed rearrangement of α,β-unsaturated enol ester (S)-2b has been used to assemble dihydropyranone (S)-3b, a material embodying the bicyclic core of the iridoid family of natural products. Elaboration of this intermediate, by chemoselective reduction followed by stereoselective β-glycosylation, has allowed the total synthesis of (-)-7-deoxyloganin (1) to be achieved in four subsequent steps. Topics: Catalysis; Esters; Heterocyclic Compounds; Iridoids; Methane; Molecular Structure; Stereoisomerism	2010

Article

Year

Concise formal synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters.

Organic & biomolecular chemistry, 2011, Dec-07, Volume: 9, Issue:23

NHC catalysed rearrangement of α,β-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated α,β-unsaturated acids provides the cyclopentapyranone core of (-)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps starting from (-)-citronellal. The elaboration to the natural product has been investigated using two new approaches. The most successful intercepts our previous work on (-)-7-deoxyloganin (1) allowing completion of a formal total synthesis in 10-steps.

Topics: Catalysis; Esters; Glycosylation; Iridoids; Isomerism; Methane; Molecular Structure; Oxidation-Reduction

2011

The total synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalyzed rearrangement of α,β-unsaturated enol esters.

Organic letters, 2010, Nov-05, Volume: 12, Issue:21

The diastereoselective N-heterocyclic carbene (NHC) catalyzed rearrangement of α,β-unsaturated enol ester (S)-2b has been used to assemble dihydropyranone (S)-3b, a material embodying the bicyclic core of the iridoid family of natural products. Elaboration of this intermediate, by chemoselective reduction followed by stereoselective β-glycosylation, has allowed the total synthesis of (-)-7-deoxyloganin (1) to be achieved in four subsequent steps.

Topics: Catalysis; Esters; Heterocyclic Compounds; Iridoids; Methane; Molecular Structure; Stereoisomerism

2010