Intermediates for the synthesis of polypropionate antibiotics

Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing

Reexamination Certificate

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C568S008000, C568S300000, C568S579000, C568S700000, C546S006000, C546S257000, C548S400000, C548S407000, C548S413000, C549S005000

Reexamination Certificate

active

11421290

ABSTRACT:
The invention relates to intermediate compounds of the formulawherein R1is H or a protecting group, R2and R3each independently represent H, methyl, or a leaving group, provided that at least one, but not both, of R2and R3is a leaving group. The intermediate compounds are useful for the synthesis of discodermolide, its derivatives, and related compounds.

REFERENCES:
patent: WO 2002/057251 (2002-07-01), None
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Ziegler, et al., “Applications sof the 3-Methyl-γ-butyrolactone Strategy to the Synthesis of Polypropionates: The Prelog-Djerassi Lactonic Ester,ent-Invictolide, and the C19-C27Fragment of Rifamycin S1,”J. Am. Chem. Soc.1988, 110(16):5442-5452.
Freemantle, Michael, “Scaled-up Synthesis of Discodermolide,” http://www.CEN-ONLINE.org, Mar. 1, 2004.
Shahid, et al., “A straightforward, highly stereoselective construction of eight stereogenic centers in (+)-discodermolide C1-C13 segment, based on a strategy of iterative aldol reactions,”Tetrahedron Letters2002, 43:6377-6381.
Choy, et al., “Simplidied Discodermolide Analogues: Synthesis and Biological Evaluation of 4-epi-7Dehydroxy-14,16-didemethyl-(+)- discodermolides as Microtubule-Stabilizing Agents,”J. Med. Chem.2003, 46:2846-2864.
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Karisalmi, et al., “Stereoselective synthesis of the C9-C19 lactone-dipropionate fragment of calyculin C,”Tetrahedron Letters2004, 45:1-4.
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