Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)

Authors
Hamamoto, H Mamedov, VA Kitamoto, M Hayashi, N Tsuboi, S
Citation
H. Hamamoto et al., Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere), TETRAHEDR-A, 11(22), 2000, pp. 4485-4497
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
22
Year of publication
2000
Pages
4485 - 4497
Database
ISI
SICI code
0957-4166(20001117)11:22<4485:CSOTCS>2.0.ZU;2-T
Abstract
Reduction of methyl 3-chloro-2-oxo-3-phenylpropanoate with various reducing agents gave syn- and anti-3-chloro-2-hydroxy-3-phenylpropanoates 3, which underwent an efficient lipase-catalyzed resolution. All four diastereomers were subsequently converted to N-benzoyl-(2R,3S)-3-phenylisoserine methyl e ster, C-13 side chain analogues of paclitaxel (Taxol). (C) 2000 Elsevier Sc ience Ltd. All rights reserved.