title: Synthesis of a paclitaxel isomer: C-2-acetoxy-C-4-benzoate paclitaxel.
abstract: A synthesis of the C-2-acetoxy-C-4-benzoate paclitaxel 2 is described. This analog has the substituents at C-2 and C-4 transposed. The key steps in the synthesis include the sequential use of Red-Al as reducing agent for the regioselective reduction of the C-2 benzoate and the C-4 acetoxy within the baccatin core. Iso-paclitaxel 2 was considerably less potent than paclitaxel in tubulin polymerization and in vitro cytotoxicity assays.
authors.affiliation: Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, CT 06492-7660, USA.
authors.forename: S H
authors.initials: SH
authors.lastname: Chen
authors.forename: V
authors.initials: V
authors.lastname: Farina
authors.forename: D M
authors.initials: DM
authors.lastname: Vyas
authors.forename: T W
authors.initials: TW
authors.lastname: Doyle
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D015195:Drug Design; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000737:chemistry; D013329:Structure-Activity Relationship; D014404:Tubulin / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D007202:Indicators and Reagents; D014404:Tubulin; D017239:Paclitaxel