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Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof

a technology which is applied in the field of analogs of discodermolide and dictyostatin1, intermediates, can solve the problems of difficult synthesizing discodermolide, difficult to ensure a sufficient supply of discodermolide, and insufficient supply of discodermolid

Inactive Publication Date: 2006-11-30
PITTSBURGH UNIV OF
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention provides a compound with a specific structure that can be used in various applications. The compound has specific groups that can be used to modify its properties, such as its solubility, reactivity, and stability. The compound can be used in various chemical reactions and can be synthesized using different methods. The technical effects of this invention include improved solubility, increased reactivity, and enhanced stability of the compound."

Problems solved by technology

Like Taxol, discodermolide is difficult to synthesize.
Unlike Taxol, discodermolide is not readily available in large quantities from natural sources.
Accordingly, assuring a sufficient supply of discodermolide is problematic.

Method used

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  • Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof
  • Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof
  • Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof

Examples

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examples

[0094] (4R)-4-Benzyl-3-[(2R,3R)-3-(tert-butyidimethylsilanyloxy)-2,4-dimethylpent-4-enoyl]oxazolidin-2-one (5). TBDMSOTf (3.44 mL, 15 mmol) was added to a stirred solution of aldol product (3.03 g, 10 mmol) and 1,6-lutidine (2.32 mL, 20 mmol) in CH2Cl2 (20 mL) at −78° C. and the mixture was stirred for 2 h at ambient temperature. The reaction was quenched by the addition of aqueous HCl (0.5 N, 50 mL). The resulting mixture was extracted with CH2Cl2 and dried over MgSO4 followed by the evaporation of solvent under reduced pressure. The product was purified by short column chromatography (hexane / EtOAc 9:1). Crude 5 was used without purification.

[0095] (2S,3R,4S,5R)-2-Allyl-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran (8). Diisobutylaluminum hydride (1.0 M in THF, 3.3 mL, 3.3 mmol) was added dropwise to a stirred solution of 7 (894 mg, 3 mmol) in anhydrous CH2Cl2 (30 mL) under an atmosphere of N2 at −78° C. and the resulting mixture was stirred for an additional 1 h at −78° ...

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Abstract

A compound of the following structure: wherein R1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe; Ra, Rb and Rc are independently an alkyl group or an aryl group; Rd is an alkyl group, an aryl group, an alkoxylalkyl group, —RiSiRaRbRc or a benzyl group, wherein Ri is an alkylene group; Re is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or —NRgRh, wherein Rg and Rh are independently H, an alkyl group or an aryl group; R3 is (CH2)n where n is and integer in the range of 0 to 5, —CH2CH(CH3)—, —CH═CH—, —CH═C(CH3)—, or —C≡C—; R4 is (CH2)p where p is an integer in the range of 4 to 12, —(CHRk1)y1(CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rs1)═C(Rs2)C(Rs3)═C(Rs4)—, —(CHRk1)y1(CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs1)CH(Rs2)C(Rs3)═C(Rs4)—, —(CHRk1)y1(CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rs1)═C(Rs2)CH(Rs3)CH(Rs4)—, —(CHRk1)y1(CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs1)CH(Rs2)CH(Rs3)CH(Rs4)—, wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4 and Rk5 are independently H, CH3, or OR2a, and Rs1, Rs2, Rs3, and Rs4 are independently H or CH3, wherein R2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe; and R5 is H or OR2b, wherein R2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS [0001] The present application claims the benefit of U.S. Provisional Patent Application Ser. No. 60 / 408,503, filed Sep. 6, 2002 and U.S. Provisional Patent Application Ser. No. 60 / 437,736 filed Jan. 2, 2003, the disclosures of which are incorporated herein by reference.GOVERNMENT INTEREST [0002] This invention was made with government support under grant CA 78039 awarded by the National Institutes of Health. The government has certain rights in this invention.BACKGROUND OF THE INVENTION [0003] The present invention relates to analogs of discodermolide and dictyostatin-1, intermediates for the synthesis of such analogs and methods of synthesis of such intermediates and analogs. [0004] References set forth herein may facilitate understanding of the present invention or the background of the present invention. Inclusion of a reference herein, however, is not intended to and does not constitute an admission that the reference is available as prio...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D313/02C07C69/73C07F9/28C07F7/02C07C33/02C07C59/10C07C59/42C07C69/732C07C69/734C07D309/10C07D309/30C07D313/00C07D319/06C07D407/06C07F7/18
CPCC07B2200/07C07C33/02C07C59/10C07C59/42C07C69/732C07F7/1852C07D309/10C07D309/30C07D313/00C07D319/06C07D407/06C07C69/734C07F7/1804
Inventor CURRAN, DENNIS P.SHIN, YOUSEUNGCHOY, NAKYENDAY, BILLY W.BALACHANDRAN, RAGHAVANMADIRAJU, CHARITHATURNER, TIFFANY
Owner PITTSBURGH UNIV OF
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