title: Preparation of phenolic paclitaxel metabolites.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, University of Kansas, Lawrence 66045, USA.
authors.forename: H
authors.initials: H
authors.lastname: Park
authors.forename: M
authors.initials: M
authors.lastname: Hepperle
authors.forename: T C
authors.initials: TC
authors.lastname: Boge
authors.forename: R H
authors.initials: RH
authors.lastname: Himes
authors.forename: G I
authors.initials: GI
authors.lastname: Georg
mesh_terms: 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
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D010636:Phenols; D014404:Tubulin; D019800:Phenol; D017239:Paclitaxel