Total synthesis of the complex taxane diterpene canataxpropellane.
Journal
Science (New York, N.Y.)
ISSN: 1095-9203
Titre abrégé: Science
Pays: United States
ID NLM: 0404511
Informations de publication
Date de publication:
07 02 2020
07 02 2020
Historique:
received:
29
07
2019
accepted:
14
01
2020
entrez:
8
2
2020
pubmed:
8
2
2020
medline:
29
4
2020
Statut:
ppublish
Résumé
Canataxpropellane belongs to the medicinally important taxane diterpene family. The most prominent congener, Taxol, is one of the most commonly used anticancer agent in clinics today. Canataxpropellane exhibits a taxane skeleton with three additional transannular C-C bonds, resulting in a total of six contiguous quaternary carbons, of which four are located on a cyclobutane ring. Unfortunately, isolation of canataxpropellane from natural sources is inefficient. Here, we report a total synthesis of (-)-canataxpropellane in 26 steps and 0.5% overall yield from a known intermediate corresponding to 29 steps from commercial material. The core structure of the (-)-canataxpropellane (
Identifiants
pubmed: 32029626
pii: 367/6478/676
doi: 10.1126/science.aay9173
doi:
Substances chimiques
Antineoplastic Agents
0
Bridged-Ring Compounds
0
Diterpenes
0
Taxoids
0
taxane
1605-68-1
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
676-681Informations de copyright
Copyright © 2020 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works.