Analogs of discodermolide and dictyostatin-1, intermediates...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

07968736

ABSTRACT:
A compound of the following structure:wherein R1is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom;R2is H, an alkyl group, an aryl 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—;R4 wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4and Rk5are independently H, CH3, or OR2a, and Rs1, Rs2, Rs3, and Rs4are independently H or CH3, wherein R2ais H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe; andR5is H or OR2b, wherein R2bis H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, —SiRaRbRc, CH2ORd, or CORe.

REFERENCES:
patent: 5430053 (1995-07-01), Pettit
patent: 7122686 (2006-10-01), Curran et al.
patent: 0680958 (1995-11-01), None
patent: WO0162239 (2001-08-01), None
patent: WO0212220 (2002-02-01), None
patent: WO02057251 (2002-07-01), None
patent: WO2004022552 (2004-03-01), None
Nerenberg, J. B. et.al. Total synthesis of the immunosuppressive agent (−)-discodermolide. J. Am. Chem. Soc. 1993, 115, 12621-12622.
Smith, A. B. et.al.;Total Synthesis of (−)-Discodermolide. J. Am. Chem. Soc. 1995, 117, 12011-12012.
Marshall, J. A. et.al.; Total synthesis of (+)-discodermolide. J. Org. Chem. 1998, 63, 7885-7892.
Paterson, I.et.al; Total synthesis of the antimicrotubule agent (+)-discodermolide using boron mediated aldol reactions of chiral ketones. Angew. Chem., Int. Ed. Eng. 2000, 39, 377-380.
Paterson, I.et.al.; Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of gamma-chiral (Z)-enals. Tetrahedron Lett. 2000, 41, 6935-6939.
Roush, W. R.et.al.; Asymmetric synthesis using tartrate modified allyl boronates. 2. Single and double asymmetric reactions with alkoxy-substituted aldehydes, J. Org. Chem. 1990, 55, 4117-4126.
Paterson, I.et.al.; A practical synthesis of (+)-discodermolide and analogues: Fragment union by complex aldol reactions. J. Am. Chem. Soc. 2001, 123, 9535-9544.
Martello, L. A. et al. The relationship between taxol and (+)-discodermolide: synthetic analogs and modeling studies. Chemistry Biol. 2001, 8, 843-855.
Harried, S. et.al. Total Synthesis of (−)-Discodermolide: An Application of a Chelation-Controlled Alkylation Reaction. J. Org. Chem. 1997, 62, 6098-6099.
Evans, D. A.et.al.. Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones. J. Am. Chem. Soc. 2002, 124, 392-393.
Pettit, G. R. et. al; Isolation and structure of the cancer cell growth inhibitor dictyostatin 1. J. Chem. Soc., Chem. Commun. 1994, 1111-1112.
CAS Online, STN, Columbus, Ohio, USA, 135: 371269, RN 374568-47-5, (2001).
Day, B. W., et.al;. Convenient syntheses of (2R,3S,4R)-3-(tert-butyldimethylsilanyloxy)-2,4-dimethy1-5-oxopentanoic acid methoxymethyl-amide from methacrolein. Preparation of C1-C7 and C17-C24 fragments of (+)-discodermolide. Tetrahedron Asymmetry 2002, 13, 1161-1165.
Clark, D. L. et. al.; Studies on the alkylation of chiral enolates: application toward the total synthesis of discodermolide. J. Org. Chem. 1993, 58 5878-5879.
Smith, A. B.. et al. Evolution of a gram-scale synthesis of (+)-discodermolide. J. Am. Chem. Soc. 2000, 122, 8654-8664.
Heathcock, C. H.et.al.;. Acyclic stereoselection-13; Aryl esters: reagents for threo-aldolization. Tetrahedron 1981, 37, 4087-4095.
Paterson, I.et.al.; A. Studies towards the total synthesis of the marine-derived immunosuppresant discodermolide: stereoselective synthesis of a C9-C24 subunit. Synlett. 1995, 498-500.
Kocovsky, P. Carbamates: a method of synthesis and some synthetic applications. Tetrahedron Lett. 1986, 27 5521-5524.
Fujiwara et. al. Synthesis of the Tetrahydropyran Part of a Marine Toxin Polycavernoside-A. Chemistry Letters. 1994, pp. 2147-2150.
CAS Online, STN, Columbus, Ohio, USA, 124: 86679, RN 172269-30-6P, (2002).
CAS Online, STN, Columbus, Ohio, USA, 66: 94583, RN 16078-24-3P, (1966).
Shin et al., Discodermolide/Dictyostatin Hybrids: Synthesis and Biological Evaluation; Organic Letters, vol. 4(25), pp. 4443-4446, 2002.
Querolle et al., Synthesis of Novel Macrocyclic Docetaxel Analogues. Influence of Their Macrocylic Ring Size on Tubulin Activity, J. Med. Chem., 46:3623-3630 (2003).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Analogs of discodermolide and dictyostatin-1, intermediates... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Analogs of discodermolide and dictyostatin-1, intermediates..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Analogs of discodermolide and dictyostatin-1, intermediates... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2674820

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.