375346-05-7Relevant articles and documents
METHOD OF SYNTHESIZING CAMPTOTHECIN-RELATING COMPOUNDS
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Page 38, (2010/02/05)
The present invention is to prepare efficiently 2'-amino-5'-hydroxypropiophenone corresponding to the AB-ring part of camptothecin (CPT) skeleton and a tricyclic ketone corresponding to the CDE-ring part in order to provide efficiently CPT by the total synthesis, which is a starting material for irinotecan hydrochloride and various kinds of camptothecin derivatives, and to provide stably CPT and its derivatives.
Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
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, (2008/06/13)
A method of synthesizing a compound having the formula: from a compound having the formula: wherein R1 is hydrogen, fluorine, chlorine or SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group —CO2H, or a benzyl group, R8 is —CO2R10, wherein R10 is an alkyl group or an aryl group, X1 is OH and X2 is H, includes the step of exposing compound (III) to at least one of an organic acid or an inorganic acid. A compound has the general formula (III).
Catalytic enantioselective synthesis of (20s)-camptothecin intermediates using cyanosilylation of ketones promoted by D-glucose-derived lanthanide catalyst
Yabu, Kazuo,Masumoto, Shuji,Kanai, Motomu,Du, Wu,Curran, Dennis P.,Shibasaki, Masakatsu
, p. 369 - 385 (2007/10/03)
An efficient catalytic enantioselective synthetic route was developed for Curran's versatile camptothecin intermediate (5). The key step is the catalytic enantioselective cyanosilylation of ketone (7) using a chiral samarium (Sm) complex. The target ketone cyanohydrin (6) was obtained with 90% ee using 2 mol % of the catalyst. A gadolinium (Gd) complex derived from the same chiral ligand could also be used as an enantioselective catalyst to synthesize Corey's intermediate (11).
MAPPICINE ANALOGS, INTERMEDIATES IN THE SYNTHESIS OF MAPPICINE ANALOGS AND METHODS OF SYNTHESIS OF MAPPICINE ANALOGS
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Page/Page column 55, (2010/02/07)
A compound having the following structure: (I) wherein Z is -CHOR1R2 or -C(O)R2; R1 is H, an alkyl group, an aryl group, -OC(O)ORa, wherein Ra is an alkyl group, -C(O)Rb wherein Rb is an alkyl group, an aryl group, an alkoxy group, an amino group, an alkylamino group, a dialkylamino group, an aryl amino group, a diarylamino group, an arylalkyl amino group, a protecting group or a fluorous tag; R2 is an alkyl group, an aryl group or an arylalkyl group; R3 is H, an alkyl group, hydroxyalkyl group or an aryl group; R4-R8 are independently the same or different and are hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, a haloalkyl group, a perfluoroalkyl group, fluorine, chlorine, bromine, a haloalkyloxy group, a carbamoyloxy group, a hydroxy group, a nitro group, a cyano group, a cyanoalkyl group, an azido group, an azidoalkyl group, a formyl group, a hydrazino group, a hydrazinoalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, -NR1Rm, wherein R1 and Rm are independently hydrogen, an alkyl group, an aryl group, an arylalkyl group, or -C(O)Rb, an aminoalkyl group, an alkylaminoalkyl group, a dialkylaminoalkyl group, an aryl aminoalkyl group, a diarylaminoalkyl group, an arylalkyl aminoalkyl group, -OC(O)ORa, wherein Ra is an alkyl group, -C(O)Rb, -SRC, S(O)Rc or S(O2)Rc wherein Rc is hydrogen, -C(O)Rb, an alkyl group, or an aryl group, (CH2)nSiRdReRf wherein n is an integer within the range of 0 through 10 and Rd, Re and Rf are independently a C1-10 alkyl group, a C2-10 alkenyl group, a C2-10 alkynyl group, an aryl group, a haloalkyl group, a cyanoalkyl group, an azidoalkyl group, a hydrazinoalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, an aminoalkyl group, an alkylaminoalkyl group, a dialkylaminoalkyl group, an aryl aminoalkyl group, a diarylaminoalkyl group, an arylalkyl aminoalkyl group. Alternatively R4 and R5, R6 and R6; R6 and R7; or R7 and R8 can form together a chain of 3 or four groups selected from CH, CH2, O, S, N, NH, N-alkyl or N-aryl. Provided that, at least one of R5-R7 is not H, a lower alkyl group, fluorine, a cyano group, a hydroxyl group, hydroxyalkyl group, an alkoxy group, an aminoalkyl group, an alkylaminoalkyl group, a dialkylaminoalkyl group, an amino group, an alkylamino group, a dialkylamino group, a carbamoyloxy group, a formyl group or -C(O)Rx wherein Rx is an alkyl group.
Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis
Zhang, Wei,Luo, Zhiyong,Chen, Christine Hiu-Tung,Curran, Dennis P.
, p. 10443 - 10450 (2007/10/03)
Solution-phase mixture synthesis has efficiency advantages and favorable reaction kinetics. Applications of this technique, however, have been discouraged by the difficulty in obtaining individual, pure final products by using conventional separation and
Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans
Gabarda, Ana E,Du, Wu,Isarno, Thomas,Tangirala, Raghuram S,Curran, Dennis P
, p. 6329 - 6341 (2007/10/03)
An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents.
