Stereoselective synthesis of (+)-boronolide and (−)-5-epi-boronolide

Stereoselective synthesis of boronolide and 5-epi-boronolide was achieved from D-(−)-tartaric acid. The key step involves the reduction of a keto Weinreb amide for the synthesis of boronolide, and a single pot construction of a diketone from the bis-Weinreb amide of tartaric acid and subsequent reduction with L-Selectride for 5-epi-boronolide

Stereoselective synthesis of (−)-6-acetoxyhexadecanolide: a mosquito oviposition attractant pheromone

The stereoselective synthesis of (−)-6-acetoxyhexadecanolide was achieved from the readily available chiral pool compound, L-(+)-tartaric acid. The synthetic sequence includes the elaboration of an α-benzyloxy aldehyde derived from tartaric acid with ring closing metathesis as the key step

Enantioselective synthesis of α\alpha-benzyloxy-ω\omega-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (-)-isolaurepan

The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan

Enantiospecific synthesis of (−)-muricatacin from L-(+)-tartaric acid

Enantiospecific synthesis of (−)-muricatacin, a bio-active lactone comprising of a 5-hydroxyalkylbutan-4-olide structural component has been achieved from L-(+)-tartaric acid. The key step involves a disteroselective reduction of a C₂-symmetric 1,4-diketone derived from tartaric acid followed by a selective Grignard reagent addition

Enantiodivergent synthesis of both enantiomers of gypsy moth pheromone disparlure

Enantiodivergent synthesis of both (−)- and (+)-disparlure, a bioactive pheromone, possessing a cis-epoxide has been accomplished. The key step involves the cross metathesis of a chiral homoallylic alcohol derived from L-(+)-tartaric acid

Enantiospecific synthesis of (−)-2-hydroxy-exo-brevicomin

An enantiospecific synthesis of (−)-2-hydroxy-exo-brevicomin was achieved from L-(+)-tartaric acid in high yield. The key step involves a very highly diastereoselective reduction of a keto Weinreb amide

An enantiospecific synthesis of (+)-hydroxy-exo-brevicomin

A concise enantiospecific synthesis of the pine beetle pheromone (+)-hydroxy-exo-brevicomin was achieved from L-(+)-tartaric acid in high yield. The key step involves the reduction of a keto-Weinreb amide derived from tartaric acid

Enantiospecific synthesis of (−)-2-hydroxy-exo-brevicomin

An enantiospecific synthesis of (−)-2-hydroxy-exo-brevicomin was achieved from l-(+)-tartaric acid in high yield. The key step involves a very highly diastereoselective reduction of a keto Weinreb amide

Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin

Enantioselective synthesis of α-hydroxy aldehydes with an alkene tether was accomplished from L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin

Microwave-assisted multicomponent reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)-thiones using lanthanum oxide as a catalyst under solvent-free conditions

An efficient synthesis of 3,4-dihydropyrimidinone derivatives using lanthanum oxide as a catalyst, from aldehydes, β-keto ester and urea/thiourea without solvent under the irradiation of microwave is described. Compared with classical Biginelli reaction conditions, this new method has the advantage of excellent yields and shorter reaction times