Total Synthesis of Paclitaxel
Shota Iiyama, Keisuke Fukaya, Yu Yamaguchi, Ami Watanabe, Hiroaki Yamamoto, Shota Mochizuki, Ryosuke Saio, Takashi Noguchi, Takeshi Oishi, Takaaki Sato, Noritaka Chida
Abstract
The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.
Topics & Concepts
OxetaneChemistryPaclitaxelEnolSilyl enol etherOlefin fiberEnol etherTotal synthesisSilylationStereochemistryEtherCombinatorial chemistryOrganic chemistryCatalysisSurgeryMedicineChemotherapyCancer Treatment and PharmacologySynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions