Analogs of dictyostatin, intermediates therefor and methods...

Details Analogs of dictyostatin, intermediates therefor and methods... Analogs of dictyostatin, intermediates therefor and methods...

2008-01-22

2008-01-22

Seaman, Margaret D. (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

11139949

ABSTRACT:
Dictyostatin and its analogs show great promise as new anticancer agents. The present invention provides dictyostatin analogs, synthetic intermediates for the synthesis of dictyostatin analogs, and synthetic methods for the synthesis of such analogs and intermediates. Dictyostatin analogs can have the following structure or its enantiomerwherein R1is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2is H, a protecting group, an alkyl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe; Ra, Rband Rcare independently an alkyl group or an aryl group; Rdis an alkyl group, an aryl group, an alkoxylalkyl group, —RiSiRaRbRcor a benzyl group, wherein Riis an alkylene group; Reis an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or —NRgRh, wherein Rgand Rhare independently H, an alkyl group or an aryl group; R3is (CH2)nwhere n is and integer in the range of 0 to 5, —CH2CH(CH3)—, —CH═CH—, —CH═C(CH3)—, or —C≡C—; R4iswherein R23ais H, a protecting group, an alkyl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe; R23bis H, a protecting group, an alkyl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe, or R23aand R23btogether form a portion of six-membered acetal ring incorporating CRtRu; Rtand Ruare independently H, an alkyl group, an aryl group or an alkoxyaryl group; and R5is H or OR2b, wherein R2bis H, a protecting group, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.

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