Simple stereocontrolled synthesis of salinosporamide A

Details Simple stereocontrolled synthesis of salinosporamide A Simple stereocontrolled synthesis of salinosporamide A

2007-02-27

2007-02-27

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

10821621

ABSTRACT:
A simple and effective stereocontrolled synthesis of salinosporamide A(1)has been developed which follows the pathway outlined in the FIGURE. The process, the first total synthesis of salinosporamide A, is capable of providing the compound in substantial quantities for further biological studies. In addition to the method of Scheme I, the present invention also includes several novel synthetic intermediate compounds, several intermediate steps of the preferred synthetic process; and the uses of these compounds in the preparation of synthetic derivatives of the compound Salinosporamide A. Salinosporamide A is of special interest as a synthetic target because of its protein in vitro cytotoxic activity against many tumor cell lines (IC50values of 10 nM or less).

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