Scinopharm Taiwan, Ltd.

Ping-Yu Wu

Julian Paul Henschke

Jyh-Hsiung Liao

Chen-Wei Lin

Tsung-Yu Hsiao

Hsyueh-Liang Wu

Wen-Hsien Wen

Chi-Nung Hsiao

This invention provides a novel method for the preparation of 2,3-disubstituted -4-oxy-cyclopentan1-one compounds that are useful for the synthesis of prostaglandins and prostaglandin analogs of industrial relevance. The method comprises the metal-catalyzed asymmetric 1,4-conjugate addition of vinylboron compounds to 2-substituted -4-oxy-cyclopent-2-en-1-ones. This method relies on the use of less toxic, easily-handled reagents, and can be performed under milder conditions than offered by some conventional methods, affording 2,3-disubstituted-4-oxy-cyclopentan-1-one compounds enantio- and diastereoselectively, which are precursors to the said prostaglandin and prostaglandin analogs, in high yield.

Metal-catalyzed asymmetric 1,4-conjugate addition of vinylboron compounds to 2-substituted-4-oxy-cyclopent-2-en-1-ones yielding prostaglandins and prostaglandin analogs

The present application discloses a stereoselective process for the preparation of &#x3b2;-C-arylglucosides that does not require the use of conventional carbohydrate protecting groups. In one embodiment, the stereoselective process comprises the preparation of the compound of formula I: the process comprising: a) contacting 1,6-anhydro-&#x3b2;-D-glucopyranose with a compound of formula II, RRRAl, in a solvent to form a first reaction mixture; b) contacting the first reaction mixture of step a) with a second reaction mixture to form a third reaction mixture, wherein the second reaction mixture is prepared by contacting an organoaluminum compound of formula III, RRAlX, with a compound of formula IV, ArM; and c) contacting the third reaction mixture with a reagent to form the compound of the formula I.

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The present invention provides processes (e.g., arylation reaction) for stereoselectively preparing C-arylglucosides that can be useful as synthetic building block or drugs, including SGLT2 inhibitors. A representative process of the present application includes the preparation of the compound of formula IV starting from a compound of the formula II with a metalated aryl compound, as disclosed below: 

Process for the preparation of &#x3b2;-C-aryl glucosides

The present invention provides efficient and economical methods for synthesis of (&#x2212;)-2-exo-morpholinoisoborne-10-thiol, its enantiomer, and related chiral catalysts. Novel compounds and methods of asymmetric synthesis are also disclosed.

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Tainan, Taiwan

Ping-Yu Wu