194420-31-0Relevant academic research and scientific papers
A CATALYTIC ASYMMETRIC METHOD FOR THE PREPARATION OF THE PACLITAXEL (TAXOL) C-13 SIDE-CHAIN DERIVATIVES AND ITS USE IN THE PREPARATION OF TAXANE DERIVATIVES
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Page/Page column 17, (2010/06/17)
A new catalytic asymmetric two-step or one-pot method for the preparation of the C-13 side-chain of paclitaxel (Taxol) and derivatives of the general formula (I) in the form of an acid, salt or ester, in which R represents an aryl group or alkyl group, R1 represents an aryl group or alkyl group, Y represents O, H or alkyl, and X1 represent -CH2-Ph, alkyl, aryl, SiR3 (where the silyl group is a common protective group) or other suitable protective group.
Highly enantioselective organocatalytic addition of aldehydes to N-(Phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues
Dziedzic, Pawel,Schyman, Patrie,Kullberg, Martin,Cordova, Armando
supporting information; experimental part, p. 4044 - 4048 (2009/12/01)
A simple highly enantioselective organocatalytic addition of aldehydes to N-(phenylmethylene)benzamides is presented. The application of (R)-proline as the catalyst and subsequent oxidation of the protected α-hydroxy-β- benzoylami-noaldehydes (92-99% ee) gives access to esterification-ready phenylisoserine derivatives such as the protected paclitaxel (taxol) side chain. Esterification of these derivatives with baccatin III gives access to the cancer chemotherapeutic substance paclitaxel and its analogues that do not exist in nature.
Asymmetric total synthesis of Taxol
Mukaiyama, Teruaki,Shiina, Isamu,Iwadare, Hayato,Saitoh, Masahiro,Nishimura, Toshihiro,Ohkawa, Naoto,Sakoh, Hiroki,Nishimura, Koji,Tani, Yu-Ichirou,Hasegawa, Masatoshi,Yamada, Koji,Saitoh, Katsuyuki
, p. 121 - 161 (2007/10/03)
The asymmetric total synthesis of Taxol was achieved by way of B to BC to ABC to ABCD ring construction. Optically active 8-membered ring enones 1 and 2 corresponding to the B ring of Taxol have been synthesized in high yields from the linear precursors 28 and 32, respectively, by intramolecular aldol cyclization using SmI2. The optically active linear polyoxy compounds 28 and 32 were obtained by way of diastereoselective aldol reaction between aldehyde 4 and ketene silyl acetal 8 catalyzed by MgBr2 · OEt2. The chiral pentanal 4 was synthesized either by asymmetric aldol reaction of achiral aldehyde 7 and ketene silyl acetal 8 by means of a chiral Lewis acid or by diastereoselective aldol reaction between the chiral aldehyde 16, derived from L-serine, and the lithium enolate derived from methyl isobutyrate. Optically active bicyclo[6.4.0]dodecanone 38β, corresponding to the BC ring system of Taxol, was prepared from 8-membered ring enone 2 in high yield by stereoselective Michael addition and successive intramolecular aldol cyclization. Furthermore, baccatin III, the ABCD ring system of Taxol, was efficiently synthesized from the BC ring system 38β by successive construction of the A and D rings by intramolecular pinacol coupling cyclization, introduction of the C-13 hydroxyl group and an oxetane-forming reaction. Finally, the total synthesis of Taxol was accomplished by dehydration condensation between a protected N-benzoylphenylisoserine 70 or 75 and 7-TES baccatin III, prepared from baccatin III. Taxol side chains 70, 73, 75, and 77, optically active protected N-benzoylphenylisoserines, were synthesized by enantioselective aldol reaction from two achiral starting materials, benzaldehyde and an enol silyl ether 65 derived from S-ethyl benzyloxyethanethioate.
Total asymmetric synthesis of taxol by dehydration condensation between 7-TES baccatin III and protected N-benzoylphenylisoserines prepared by enantioselective aldol reaction
Shiina, Isamu,Saitoh, Katsuyuki,Frechard-Ortuno, Isabelle,Mukaiyama, Teruaki
, p. 3 - 4 (2007/10/03)
Total asymmetric synthesis of Taxol was completed by dehydration condensation between a protected N-benzoylphenylisoserine 4 or 9 and 7-TES baccatin in which was prepared from 8-membered ring enone. Taxol side chains 4, 7, 9 and 11, optically active protected N-benzoylphenylisoserines, were successfully synthesized by enantioselective aldol reaction from two achiral starting materials, benzaldehyde and an enol silyl ether derived from S-ethyl benzyloxyethanethioate.
