Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol.
Russell, David A
Freudenreich, Julien J
Stewart, Hannah L
Bond, Andrew D
Sore, Hannah F
Spring, David R
Org Biomol Chem
Royal Society of Chemistry (RSC)
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Russell, D. A., Freudenreich, J. J., Stewart, H. L., Bond, A. D., Sore, H. F., & Spring, D. R. (2018). Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol.. Org Biomol Chem, 16 (35), 6395-6398. https://doi.org/10.1039/c8ob01919c
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).
Engineering and Physical Sciences Research Council (EP/J016012/1)
Engineering and Physical Sciences Research Council (EP/P020291/1)
External DOI: https://doi.org/10.1039/c8ob01919c
This record's URL: https://www.repository.cam.ac.uk/handle/1810/285443