Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 35, 2018
Previous Article Next Article

Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol

Author affiliations

Abstract

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).

Graphical abstract: Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol

Back to tab navigation

Supplementary files

Article information


Submitted
06 Aug 2018
Accepted
21 Aug 2018
First published
22 Aug 2018

Org. Biomol. Chem., 2018,16, 6395-6398
Article type
Communication

Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol

D. A. Russell, J. J. Freudenreich, H. L. Stewart, A. D. Bond, H. F. Sore and D. R. Spring, Org. Biomol. Chem., 2018, 16, 6395
DOI: 10.1039/C8OB01919C

Social activity

Search articles by author

Spotlight

Advertisements