Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization

Keisuke Fukaya; Yuta Tanaka; Ayako C Sato; Keisuke Kodama; Hirohisa Yamazaki; Takeru Ishimoto; Yasuyoshi Nozaki; Yuki M Iwaki; Yohei Yuki; Kentaro Umei; Tomoya Sugai; Yu Yamaguchi; Ami Watanabe; Takeshi Oishi; Takaaki Sato; Noritaka Chida

doi:10.1021/acs.orglett.5b01173

Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization

Org Lett. 2015 Jun 5;17(11):2570-3. doi: 10.1021/acs.orglett.5b01173. Epub 2015 May 26.

Authors

Affiliations

¹ †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
² ‡School of Medicine, Keio University, 4-1-1 Hiyoshi, Kohoku-ku, Yokohama 223-8521, Japan.

PMID: 26010812
DOI: 10.1021/acs.orglett.5b01173

Abstract

A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Antineoplastic Agents, Phytogenic / chemistry
Cyclization
Molecular Conformation
Paclitaxel / chemical synthesis*
Paclitaxel / chemistry
Proteins / chemistry*
Stereoisomerism

Substances

Antineoplastic Agents, Phytogenic
Proteins
sperm motility inhibitor 2
Paclitaxel