Preparation of phenolic paclitaxel metabolites.
The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3'-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)-baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.
Park
H
H
Department of Medicinal Chemistry, University of Kansas, Lawrence 66045, USA.
Hepperle
M
M
Boge
T C
TC
Himes
R H
RH
Georg
G I
GI
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D017239:Paclitaxel / Q000737:chemistry / Q000378:metabolism*; D019800:Phenol; D010636:Phenols / Q000378:metabolism*; D014404:Tubulin / Q000187:drug effects; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D010636:Phenols; D014404:Tubulin; D019800:Phenol; D017239:Paclitaxel