Purdue Research Foundation

Akanocure Phamraceuticals, Inc.

Akanocure Pharmaceuticals, Inc.

Fuchs, Philip L.

Noshi, Mohammad N.

Philip L Fuchs

Mohammad N Noshi

Douglas A Lantrip

Jin Luo

David J Meyers

In C Kim

Seongmin Lee

Taesik Park

Yuzhong Chen

Eduardo Torres

Jerry B Evarts, Jr

The present technology is directed to polypropionate lactone stereotetrads of Formula (I) (or a pharmaceutically acceptable salt and/or solvate thereof) which are significant intermediates for multiple synthetic applications.

Scalable polypropionate lactone stereotetrads

The present technology is directed to polypropionate lactone stereotetrads of Formula (I) (or a pharmaceutically acceptable salt and/or solvate thereof) which are significant intermediates for multiple synthetic applications. 

The invention provides novel six and seven-carbon termini-differentiated polypropionate stereotetrads and stereopentads useful in syntheses of natural products. The invention also provides a novel alkylative sulfenylation-desulfonylation process that efficiently transforms enantiopure epoxyvinyl sulfones to syn and anti dienylsulfides in two operations.

Chemical synthons and intermediates

The invention provides a catalytic, chemospecific and stereospecific method of oxidizing a wide variety of substrates without unwanted side reactions. Essentially, the method of the instant invention, under relatively mild reaction conditions, catalytically, stereospecifically and chemospecifically inserts oxygen into a hydrocarbon C&#x2014;H bond. Oxidation (oxygen insertion) at a tertiary C&#x2014;H bond to form an alcohol (and in some cases a hemiacetal) at the tertiary carbon is favored. The stereochemistry of an oxidized tertiary carbon is preserved. Ketones are formed by oxidizing a secondary C&#x2014;H bond and ring-cleaved diones are formed by oxidizing cis tertiary CH bonds.

Catalytic oxidation of C&#x2014;H bonds

Novel folic acid derivatives and their use in preparation of &ggr;-esters of folic acid via a pteroyl azide intermediate are described. Folic acid &ggr;-esters are useful intermediates in the synthesis of folic acid conjugates capable of binding folate receptors in vitro and in vivo.

Folic acid derivatives

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West Lafayette, IN, United States of America

Philip L Fuchs