Journal
CHEMISTRY AND PHYSICS OF LIPIDS
Volume 163, Issue 2, Pages 165-171Publisher
ELSEVIER IRELAND LTD
DOI: 10.1016/j.chemphyslip.2009.10.012
Keywords
Allylic oxidation; Oxyfunctionalization; Cytochrome P-450; Hydroxylation; Ketonization; Triterpenoid; Unactivated C-H bond
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Funding
- Nihon University Multidisciplinary Research
- Institute of Natural Sciences Nihon University
- Ministry of Education, Sciences, Sports, and Culture of Japan
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A system consisting of meso-5,10,15,20-tetramesitylporphyrinate osmium(II) carbonyl complex [Os(TMP)CO] as a precatalyst and tert-butylhydroperoxide (TBHP) as an oxygen donor is shown to be an efficient, regioselective oxidant system for the allylic oxidation, ketonization and hydroxylation of unactivated C-H bonds in a series of the peracetate derivatives of penta- and tetracyclic triterpenoids. Treatment of the substrates with this oxidant system afforded a variety of novel or scarce oxygenated derivatives in one-step. Structures of the isolated components, after chromatographic separation, were determined by spectroscopic methods including GC-MS and shift-correlated 2D-NMR techniques. Factors governing the regioselectivity and the possible mechanism for the oxyfunctionalization of the unactivated carbons are also discussed. (C) 2009 Elsevier Ireland Ltd. All rights reserved.
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