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US 8,809,558 B1Granted
Synthetic methods and intermediates for the preparation of xenicanes
AssigneeRutgers, The State University of New Jersey
InventorsLawrence J. Williams, Michael Drahl, Madhuri Manpadi
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Abstract
The invention provides novel synthetic intermediates and synthetic methods that are useful for preparing compounds of the xenicane family. Certain compounds of the invention may also possess anti-cancer properties.
Claims3
A compound of formula 1:
- wherein:
- Ra is H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl(C1-C6)alkyl, aryl, or heteroaryl, wherein each (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)cycloalkyl, and (C3-C8)cycloalkyl(C1-C6)alkyl of Ra is optionally substituted with one or more groups independently selected from halo, hydroxy, cyano, nitro, (C1-C6)alkoxy, (C3-C8)cycloalkyl, oxo, carboxy, aryl, aryloxy, and —NRbRc;
- and wherein each aryl, and heteroaryl of Ra is optionally substituted with one or more groups independently selected from (C1-C6)alkyl, halo, hydroxy, cyano, carboxy, nitro, trifluoromethyl, trifluoromethoxy, (C1-C6)alkoxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkanoyloxy, and —NRbRc;
- and
- Rb and Rc are each independently selected from H, (C1-C6)alkyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl(C1-C6)alkyl, aryl, heteroaryl, aryl(C1-C6) alkyl and heteroaryl(C1-C6)alkyl;
- or Rb and Rc together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino.
3 more elements
A method for preparing an ester of formula 1:
- wherein Ra is methyl;
- comprising treating an acid of formula 2:
- with (Me)2SiCHN2 in methanol at about 0° C. to provide the ester of formula 1.
A compound of formula 2, 10, 11b, 12, 13, 20, 23, 24, 25, 26, or 27:
Dependencies are inferred from the claim text.