We describe semi-syntheses of the 11-hydroxyrotenoids sumatrol (1) and villosinol (2), starting from rotenone (5), using an oxime-directed C11-H functionalisation approach. Thus, rotenone (5) was converted into rotenone oxime (6), which gave dimeric palladacycle 7 following reaction with Na2PdCl4·3H2O. Controlled, divergent, oxidation of palladacycle 7 with either Pb(OAc)4 or K2Cr2O7 afforded the 11-acetoxylated intermediates 9 and 13, respectively, which were transformed into sumatrol (1) and villosinol (2).
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8ob01919c | DOI Listing |
Publication Analysis
Top Keywords
sumatrol villosinol
12
semi-syntheses 11-hydroxyrotenoids
8
11-hydroxyrotenoids sumatrol
8
villosinol describe
4
describe semi-syntheses
4
villosinol starting
4
starting rotenone
4
rotenone oxime-directed
4
oxime-directed c11-h
4
c11-h functionalisation
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!