Total Synthesis of Paclitaxel

Iiyama, Shota; Fukaya, Keisuke; Yamaguchi, Yu; Watanabe, Ami; Yamamoto, Hiroaki; Mochizuki, Shota; Saio, Ryosuke; Noguchi, Takashi; Oishi, Takeshi; Sato, Takaaki; Chida, Noritaka

doi:10.1021/acs.orglett.1c03851.s001

Total Synthesis of Paclitaxel

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posted on 2021-12-14, 14:34 authored by Shota Iiyama, Keisuke Fukaya, Yu Yamaguchi, Ami Watanabe, Hiroaki Yamamoto, Shota Mochizuki, Ryosuke Saio, Takashi Noguchi, Takeshi Oishi, Takaaki Sato, Noritaka Chida

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.

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double rubottom oxidation 13 hydroxy groups total synthesis tetracyclic framework step operation novel ag bridgehead olefin

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Total Synthesis of Paclitaxel

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