Issue 35, 2018

Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol

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

Supplementary files

Article information

Article type
Communication
Submitted
06 Aug. 2018
Accepted
21 Aug. 2018
First published
22 Aug. 2018

Org. Biomol. Chem., 2018,16, 6395-6398

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

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