- 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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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.
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Page/Page column 18
(2010/06/17)
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- Highly enantioselective organocatalytic addition of aldehydes to N-(Phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues
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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.
- Dziedzic, Pawel,Schyman, Patrie,Kullberg, Martin,Cordova, Armando
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supporting information; experimental part
p. 4044 - 4048
(2009/12/01)
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- Highly stereocontrolled asymmetric syntheses of taxol and taxotere C-13 side chain analogues
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Asymmetric aldol reaction of (+)-tricarbonyl(η6-2-trimethylsilylbenzaldehyde)chromium(0) complex (4) with titanium enolate of S-tert-butyl benzyloxyethanethioate (10) provided, after consecutive desilylation and decomplexation, anti-aldol product 15 in a highly stereo selective manner. Anti-product 15 was subsequently converted to (2R,3S)-N-benzoyl- and N-tert-butoxycarbonyl-3-phenylisoserine methyl esters (23 and 24), C-13 side chain analogues of taxol (1) and taxotere (2).
- Mukai, Chisato,Kim, In Jong,Furu, Etsuko,Hanaoka, Miyoji
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p. 8323 - 8336
(2007/10/02)
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- An optically active chromium(0)-complexed benzaldehyde in organic synthesis: A highly stereocontrolled asymmetric synthesis of (2R,3S)-(-)-N-benzoyl-3-phenylisoserine methyl ester, the taxol C-13 side chain analogue
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An asymmetric aldol reaction of (+)-chromium(0)-complexed benzaldehyde 4 with the titanium enolate generated from the ethanethioate 5 provided the anti-aldol product 6 in a highly stereoselective manner, which was subsequently converted to the taxol C-13 side chain.
- Mukai,Kim,Hanaoka
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p. 1007 - 1010
(2007/10/02)
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