Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol.
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Peer-reviewed
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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).
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0601 Biochemistry and Cell Biology
Journal Title
Org Biomol Chem
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Journal ISSN
1477-0520
1477-0539
1477-0539
Volume Title
16
Publisher
Royal Society of Chemistry (RSC)
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Engineering and Physical Sciences Research Council (EP/J016012/1)
Engineering and Physical Sciences Research Council (EP/P020291/1)
Engineering and Physical Sciences Research Council (EP/P020291/1)