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

Authors :
Fukaya K
Tanaka Y
Sato AC
Kodama K
Yamazaki H
Ishimoto T
Nozaki Y
Iwaki YM
Yuki Y
Umei K
Sugai T
Yamaguchi Y
Watanabe A
Oishi T
Sato T
Chida N
Source :
Organic letters [Org Lett] 2015 Jun 05; Vol. 17 (11), pp. 2570-3. Date of Electronic Publication: 2015 May 26.
Publication Year :
2015

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.

Details

Language :
English
ISSN :
1523-7052
Volume :
17
Issue :
11
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
26010812
Full Text :
https://doi.org/10.1021/acs.orglett.5b01173