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ASYMMETRIC-SYNTHESIS OF THE TAXOL AND TAXOTERE C-13 SIDE-CHAINS

Abstract:

A practical and efficient asymmetric synthesis of the 3-benzoylamino-2- hydroxy-3-phenylpropionic acid derived side chain of the important anticancer agent taxol is described. The pivotal synthetic transformation relies upon the highly diastereoselective tandem lithium amide conjugate addition-electrophilic hydroxylation of tert-butyl cinnamate 4. The resultant anti β-amino- α-hydroxy acid derivative is readily converted to the anti diastereoisomer of the taxol side chain methyl ester, from w...

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Publication status:
Published

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Publisher copy:
10.1039/p19940002385

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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
17
Pages:
2385-2391
Publication date:
1994-09-07
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
URN:
uuid:49c0a57f-a662-4f4b-ab02-46f16d62e4b2
Source identifiers:
110863
Local pid:
pubs:110863
Language:
English

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