Publication

Synthesis of a polyhydroxyquinolizidine bearing a polyhydroxylated carbon side-chain

Pierre Vogel
1999
Journal Articles

Abstract

The lithium enolate of (-)-6-endo-chloro-5-exo-(phenyl-seleno)-7-oxabicyclo[2.2.1]heptan-2-one ((-)-4) added to (+)-(3aR, 4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2, 3-d]isoxazole-3-carbaldehyde ((+)-5) giving a major aldol (+)-6 in 90% yield that was converted into (+)-(1R,4R,5R, 6S,7R)-4-exo-(4-bromobenzenesulfonyloxy)-6-exo-{(S)-[(tert-butyl)dimethy lsilyloxy]-[(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]di oxolo[4,5]furo [2,3-d]isoxazol-3-yl]methyl}-7-endo-(methoxymethoxy)-2,8-dioxabicyclo[3. 2.1]octan-3-one ((+)-15). Methanolysis of (+)-15, followed by reduction and protection steps provided (-)-1,4-anhydro-3-{6S-5-[(benzyloxy) carbonyl]amino-5-deoxy-beta-L-idohexofuranos-6-C-yl}-3-deoxy-2,6-bis-O-( methoxymethyl)-alpha-D-galactopyranose((-)-21). Acidic treatment of(-)-21 followed by catalytical hydrogenation generated (-)-(1R,2R,3S,7R,8S,9S,9aS)-1,3,4,6,7,8,9a-octahydro-8-[(1'R,2'R)-1',2', 3'-trihydroxypropyl]-2H-quinolizine-1,2,3,7,9-pentol((-)-2) characterized as its octaacetate (+)-26.

Official source

https://infoscience.epfl.ch/entities/publication/1b115c0e-7de8-4fb9-885d-30a0763692b5

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Pierre Vogel
1999
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/1b115c0e-7de8-4fb9-885d-30a0763692b5

About this result

Related concepts (9)

Hydrogenation

Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures.

Transfer hydrogenation

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular . It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis.

Asymmetric hydrogenation

Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information (what chemists refer to as chirality) to transfer from one molecule to the target, forming the product as a single enantiomer.