Katsuya Matsumoto

Synthesis of (+)-trans-Whisky Lactone, (+)-trans-Cognac Lactone and (+)-Eldanolide

A new and useful synthesis of (+)-trans-whisky lactone (3), (+)-trans-cognac lactone (4) and (+)-eldanolide (5) starting from levoglucosenone (1) is described

Synthesis of (+)-trans-whisky lactone, (-)-cis-whisky lactone, (+)-cognac lactone and (+)-eldanolide

(+)-trans-Whisky lactone (5) and (-)-cis-whisky lactone (8), (+)-cognac lactone (9) and (+)-eldanolide (10) were synthesized starting from levoglucosenone (1) in optically pure states

Stereoselectivities in the coupling reaction between silytated pyrimidine bases and 1-halo-2,3-dideoxyribose

Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines have been examined from the point of stereoselectivity. When the reaction was carried out in chloroform, the selectivity was in the anomeric ratio of α:β=4:6. On the other hand, the presence of tertiary amine raises the selectivity to α:β=3:7

Nucleoside synthesis from furanoid glycals

Reaction of furanoid glycals with PhSCl afforded 1-chlorosugars, which were used for condensation reaction with silylated uracil in the presence of SnCl4. These two reactions proceeded in a highly stereoselective manner

NOVEL SYNTHESIS OF PHYTOSPHINGOSINE FROM LEVOGLUCOSENONE

Abstract Phytosphingosine, (2 S ,3 S ,4 R )-2-amino-1,3,4-octadecanetriol was prepared in 8.6% overall yield in 17 steps from levoglucosenone (1,6-anhydro-3,4-dideoxy-β- d - glycero -hex-3-enopyranos-2-ulose) by reduction of the carbonyl group, selective cis -oxyamination of the carbon-carbon double bond, oxidation of the 2-hydroxyl group to the carbonyl group, regioselective Baeyer-Villiger oxidation, reduction of the afforded lactone to the linear amino alcohol, oxidation of the primary hydroxyl group to the aldehyde, introduction of the hydrocarbon chain using a Wittig reaction, hydrogenation of the resulting carbon-carbon double bond, and deprotection.

Synthesis of 1,6:3,4-Dianhydro-b-D-talopyranose from Levoglucosenone: Epoxidation of Olefin via trans-Iodoacetoxylation

Levoglucosenone (1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose, 1) was converted to give 1,6:3,4-dianhydro-β-D-talopyranose (8) in good yield through stereoselective trans-iodoacetoxylation followed by basic hydrolysis

Novel synthesis of 3-acetamido-3-deoxy- and 4-acetamido-4-deoxy-d-altrose from levoglucosenone using regioselective cis-oxyamination

Abstract Two rare amino sugars, 3-acetamido-3-deoxy- and 4-acetamido-4-deoxy- d -altrose, were prepared from levoglucosenone (1,6-anhydro-3,4-dideoxy-β- d - glycero -hex-3-enopyranos-2-ulose) respectively by reduction of the carbonyl group, selective cis -oxyamination of the carbon-carbon double bond, detosylation of the p -toluenesulfonamido group, acetylation, acetolysis of the 1,6-anhydro bond, and finally deacetylation of the O -acetyl groups. The regioselectivity in cis -oxyamination of the carbon-carbon double bond of allylic alcohol obtained by reduction of levoglucosenone could be controlled by the choice of the protecting groups of the allylic hydroxyl group.

Condensation Reaction Between 2,2-Diphenylthio-2,3-Dideoxyribose and Silylated Pyrimidine Bases

Abstract The condensation reaction between 2,2-diphenylthio-2,3-dideoxyribose and silylated pyrimidine bases was examined. In the presence of TMSOTf as a catalyst, this reaction proceeded to give the nucleosides in the ratio of α: β = 2:8. Each β-anomer was converted to protected 2′,3′-dideoxynucleosides.

Synthesis of (2S, 4S)-2-hydroxy-4-hydroxymethyl-4-butanolide, a hunger substance

(2S,4S)-2-Hydroxy-4-hydroxymethyl-4-butanolide (1a), which is a hunger substance, was synthesized stereoselectively starting from D-γ-ribono-1,4-lactone (2)