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Issue 35, 2018
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Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol

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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).

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

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Publication details

The article was received on 06 Aug 2018, accepted on 21 Aug 2018 and first published on 22 Aug 2018


Article type: Communication
DOI: 10.1039/C8OB01919C
Citation: Org. Biomol. Chem., 2018,16, 6395-6398
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    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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