The invention is directed to a method to reduce a C—C double bond of an enone of a steroidal compound to produce a mixture of β ketone product and α ketone product, comprising treating a solution or suspension of the steroidal compound in a solvent with hydrogen gas in the presence of a catalyst and
The invention is directed to a method to reduce a C—C double bond of an enone of a steroidal compound to produce a mixture of β ketone product and α ketone product, comprising treating a solution or suspension of the steroidal compound in a solvent with hydrogen gas in the presence of a catalyst and a substituted pyridine.
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1. A method of reducing the C—C double bond of an enone of a steroidal compound to produce a mixture of β ketone product and α ketone product, the method comprising treating a solution or suspension of the steroidal compound in a solvent with hydrogen gas in the presence of a catalyst and a substitu
1. A method of reducing the C—C double bond of an enone of a steroidal compound to produce a mixture of β ketone product and α ketone product, the method comprising treating a solution or suspension of the steroidal compound in a solvent with hydrogen gas in the presence of a catalyst and a substituted pyridine. 2. The method of claim 1, wherein an excess of the β ketone product is produced compared to the α ketone product. 3. The method of claim 1, wherein the ratio of the β ketone product to the α ketone product is at least 2:1. 4. The method of claim 1, wherein the ratio of the β ketone product to the α ketone product is at least 10:1. 5. The method of claim 1, wherein the ratio of the β ketone product to the α ketone product is at least 20:1. 6. The method of claim 1, wherein the ratio of the β ketone product to the α ketone product is at least 50:1. 7. The method of claim 1, wherein the substituted pyridine is a 3-substituted pyridine. 8. The method of claim 7, wherein the 3-substituted pyridine is selected from 3-picoline, 3-methoxypyridine, 3-ethylpyridine, 3-n-butylpyridine, 3-isobutylpyridine, 3-hydroxypyridine, 3-aminopyridine, and 3-dimethylaminopyridine. 9. The method of claim 7, wherein the 3-substituted pyridine is 3-picoline. 10. The method of claim 1, wherein the catalyst is a palladium catalyst. 11. The method of claim 1, wherein the solvent comprises the substituted pyridine. 12. The method of claim 11, wherein the solvent comprises 3-picoline. 13. A method of making a mixture of compounds of formulae II and III: or a pharmaceutically acceptable salt thereof, wherein: n is 0 or 1;R30 is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, heteroaralkyl, haloalkyl, —OR31, —C(O)R31, —CO2R31, —SO2R31, —C(O)N(R31)(R31), —[C(R)2]q—R31, —[(W)—N(R)C(O)]qR31, —[(W)—C(O)]qR31, —[(W)—C(O)O]qR31, —[(W)—OC(O)]qR3, —[(W)—SO2]qR31, —[(W)N(R31)SO2]qR31, —[(W)—C( O)N(R31)]qR31, —[(W)—O]qR31, —[(W)—N(R)]qR31, —W—(NR31)3+X− or —[(W)—S]qR31;W, at each occurrence, independently is an alkylene group;q, at each occurrence, independently is 1, 2, 3, 4, 5, or 6;X− is a halide;R31, at each occurrence, independently is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, heteroaralkyl or —[C(R)2]p—R32;or any two occurrences of R31 taken together with the atom to which they are bound form an optionally substituted 4-8 membered ring that contains 0-3 heteroatoms selected from N, O and S;p is 0-6;each R32 is independently hydroxyl, —N(R)COR, —N(R)C(O)OR, —N(R)SO2(R), —C(O)N(R)2, —OC(O)N(R)(R), —SO2N(R)(R), —N(R)(R), —COOR, —C(O)N(OH)(R), —OS(O)2OR, —S(O)2OR, —OP(O)(OR)(OR), —NP(O)(OR)(OR), or —P(O)(OR)(OR); and each R is independently H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl or aralkyl; the method comprising treating a solution or suspension of compound of formula IV: or a pharmaceutically acceptable salt thereof, in a solvent with hydrogen gas in the presence of a catalyst and a substituted pyridine. 14. The method of claim 13, wherein an excess of the compound of formula II is produced compared to the compound of formula III. 15. The method of claim 13, wherein the ratio of the compound of formula II to compound of formula III is at least 10:1. 16. The method of claim 13, wherein the ratio of the compound of formula II to compound of formula III is at least 20:1. 17. The method of claim 13, wherein the substituted pyridine is a 3-substituted pyridine. 18. The method of claim 17, wherein the 3-substituted pyridine is 3-picoline. 19. The method of claim 13, wherein the solvent comprises the substituted pyridine. 20. The method of claim 19, wherein the solvent comprises 3-picoline. 21. The method of claim 13, wherein the catalyst is a palladium catalyst. 22. The method of claim 13, wherein n is 1. 23. The method of claim 22, wherein R30 is H. 24. The method of claim 13, wherein the compounds of formulae II and III have the following absolute chemistry:
Adams, Julian; Castro, Alfredo C.; Foley, Michael A.; Janardanan Nair, Somarajan Nair; Nevalainen, Marta; Porter, James R.; Tremblay, Martin R., Cyclopamine analogues and methods of use thereof.
Adams, Julian; Castro, Alfredo C.; Foley, Michael A.; Janardanannair, Somarajannair; Nevalainen, Marta; Porter, James R.; Tremblay, Martin R., Cyclopamine analogues and methods of use thereof.
Adams,Julian; Castro,Alfredo C.; Foley,Michael A.; Janardanan Nair,Somarajan Nair; Nevalainen,Marta; Porter,James R.; Tremblay,Martin R., Cyclopamine analogues and methods of use thereof.
Adams,Julian; Castro,Alfredo C.; Foley,Michael A.; Janardanan Nair,Somarajan Nair; Nevalainen,Marta; Porter,James R.; Tremblay,Martin R., Cyclopamine analogues and methods of use thereof.
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Rudnicki, Michael; Seale, Patrick; Polesskaya, Anna; Fortin, Anouk, Growth and differentiation of adult muscle stem cells with activators or inhibitors of Wnt signaling.
Porter, Jeffrey; Guicherit, Oivin M.; Rubin, Lee; Baxter, Anthony David; Boyd, Edward Andrew; Price, Stephen, Small organic molecule regulators of cell proliferation.
Austad, Brian; Behnke, Mark L.; Castro, Alfredo C.; Grogan, Michael J.; Janardanannair, Somarajannair; Lescarbeau, Andre; Peluso, Stephane; Charette, Andre B.; Tremblay, Martin R., Cyclopamine analogs.
Austad, Brian; Behnke, Mark L.; Castro, Alfredo C.; Grogan, Michael J.; Janardanannair, Somarajannair; Lescarbeau, Andre; Peluso, Stephane; Charette, Andre B.; Tremblay, Martin R., Cyclopamine analogs.
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