专利号:US-5212317-A 优先权日:1990-12-20 标 题:Methods and intermediates for the assymmetric synthesis of camptothecin and camptothecin analogs 发明人:COMINS DANIEL L; BAEVSKY MATTHEW F 权利人:UNIV NORTH CAROLINA STATE 摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a moiety of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.
专利号:US-5258516-A 优先权日:1990-12-20 标题 :Optically pure D,E ring intermediates useful for the synthesis of camptothecin and camptothecin analogs 发明人:COMINS DANIEL L; BAEVSKY MATTHEW F 权利人:NC STATE UNIVERSITY 摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 ; tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.
专利号:US-5254690-A 优先权日:1990-12-20 标 题 :Alkoxymethylpyridine d-ring intermediates useful for the synthesis of camptpthecin and camptothecin analogs 发明人:COMINS DANIEL L; BAEVSKY MATTHEW F 权利人:UNIV NORTH CAROLINA STATE 摘要:Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R 1 may be H, loweralkyl, loweralkoxy, or halo; R 2 , R 3 , R 4 , and R 5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.
专利号:US-5264579-A 优先权日:1990-12-20 标 题 :D ring intermediates for the synthesis of camptothecin and camptothecin analogs 发明人:COMINS DANIEL L; BAEVSKY MATTHEW F 权利人:UNIV NORTH CAROLINA STATE 摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, and Y is H, F or Cl, are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.
专利号:US-5315007-A 优先权日:1990-12-20 标 题:Process for making DE ring intermediates for the synthesis of camptothecin and camptothecin analogs 发明人:COMINS DANIEL L; BAEVSKY MATTHEW F 权利人:UNIV NORTH CAROLINA STATE 摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.
专利号:US-7074932-B2 优先权日:1999-06-24 标题 :Preparation of quinoline-substituted carbonate and carbamate derivatives 发明人:ALLEN MICHAEL S; PREMCHANDRAN RAMIYA H; CHANG SOU-JEN; CONDON STEPHEN; DEMATTEI JOHN A; KING STEVEN A; KOLACZKOWSKI LAWRENCE; MANNA SUKUMAR; NICHOLS PAUL J; PATEL HEMANT H; PATEL SUBHASH R; PLATA DANIEL J; STONER ERIC J; TIEN JIEN-HEH J; WITTENBERGER STEVEN J 权利人:ALLEN MICHAEL S; PREMCHANDRAN RAMIYA H; CHANG SOU-JEN; CONDON STEPHEN; DEMATTEI JOHN A; KING STEVEN A; KOLACZKOWSKI LAWRENCE; MANNA SUKUMAR; NICHOLS PAUL J; PATEL HEMANT H; PATEL SUBHASH R; PLATA DANIEL J; STONER ERIC J; TIEN JIEN-HEH J; WITTENBERGER STEVEN J 摘要:The invention relates to a process for preparing quinoline-substituted carbonate and carbamate compounds, which are important intermediates in the synthesis of 6-O-substituted macrolide antibiotics. The process employs metal-catalyzed coupling reactions to provide a carbonate or carbamate of formula (I) or (II) or a substrate that can be reduced to obtain the same.
摘要:Chen, C.; Yu, L., Science of Synthesis Knowledge Updates, (2019) 3, 124. 摘要:Silva, V. L. M.; Pinto, D. C. G. A.; Santos, C. M. M.; Rocha, D. H. A., Science of Synthesis Knowledge Updates, (2022) 3, 377. 摘要:Beier, P., Science of Synthesis Knowledge Updates, (2014) 2, 320. 摘要:Littke, A., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2012) 1, 210. 摘要:Arévalo, M. J.; Lavilla, R., Science of Synthesis: Multicomponent Reactions, (2013) 1, 311.