Synthesis of paclitaxel. 2. construction of the ABCD ring and formal synthesis

Keisuke Fukaya, Keisuke Kodama, Yuta Tanaka, Hirohisa Yamazaki, Tomoya Sugai, Yu Yamaguchi, Ami Watanabe, Takeshi Oishi, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A formal synthesis of the antitumor diterpenoid paclitaxel (Taxol) is described. The ABC ring of paclitaxel, synthesized starting from 1,3-cyclohexanedione and tri-O-acetyl-d-glucal by SmI<inf>2</inf>-mediated cyclization as the key transformation, was successfully converted to Takahashi's tetracyclic oxetane intermediate. A double Chugaev reaction was employed for introduction of the strained bridgehead olefin, and stereoselective formation of the oxetane ring afforded the known synthetic intermediate, completing the formal synthesis of paclitaxel.

Original languageEnglish
Pages (from-to)2574-2577
Number of pages4
JournalOrganic Letters
Volume17
Issue number11
DOIs
Publication statusPublished - 2015 Jun 5

Fingerprint

Paclitaxel
rings
synthesis
alkenes
Diterpenes
Cyclization
Alkenes
oxetane

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Fukaya, K., Kodama, K., Tanaka, Y., Yamazaki, H., Sugai, T., Yamaguchi, Y., ... Chida, N. (2015). Synthesis of paclitaxel. 2. construction of the ABCD ring and formal synthesis. Organic Letters, 17(11), 2574-2577. https://doi.org/10.1021/acs.orglett.5b01174

Synthesis of paclitaxel. 2. construction of the ABCD ring and formal synthesis. / Fukaya, Keisuke; Kodama, Keisuke; Tanaka, Yuta; Yamazaki, Hirohisa; Sugai, Tomoya; Yamaguchi, Yu; Watanabe, Ami; Oishi, Takeshi; Satou, Takaaki; Chida, Noritaka.

In: Organic Letters, Vol. 17, No. 11, 05.06.2015, p. 2574-2577.

Research output: Contribution to journalArticle

Fukaya, K, Kodama, K, Tanaka, Y, Yamazaki, H, Sugai, T, Yamaguchi, Y, Watanabe, A, Oishi, T, Satou, T & Chida, N 2015, 'Synthesis of paclitaxel. 2. construction of the ABCD ring and formal synthesis', Organic Letters, vol. 17, no. 11, pp. 2574-2577. https://doi.org/10.1021/acs.orglett.5b01174
Fukaya K, Kodama K, Tanaka Y, Yamazaki H, Sugai T, Yamaguchi Y et al. Synthesis of paclitaxel. 2. construction of the ABCD ring and formal synthesis. Organic Letters. 2015 Jun 5;17(11):2574-2577. https://doi.org/10.1021/acs.orglett.5b01174
Fukaya, Keisuke ; Kodama, Keisuke ; Tanaka, Yuta ; Yamazaki, Hirohisa ; Sugai, Tomoya ; Yamaguchi, Yu ; Watanabe, Ami ; Oishi, Takeshi ; Satou, Takaaki ; Chida, Noritaka. / Synthesis of paclitaxel. 2. construction of the ABCD ring and formal synthesis. In: Organic Letters. 2015 ; Vol. 17, No. 11. pp. 2574-2577.
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