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Iron(III)picolinate-induced oxygenation and subsequent rearrangement of triterpenoid derivatives with hydrogen peroxide



Iron(III)picolinate-induced oxygenation and subsequent rearrangement of triterpenoid derivatives with hydrogen peroxide



Chemical & Pharmaceutical Bulletin 48(1): 120-125



The reaction of oleanane triterpenoid 1b with a FeIII(PA; picolinate)3/H2O2/MeCN system (reagent system A), a simple model system for mono-oxygenase, gave the 11alpha-hydroxyl derivative 3 as major product, along with 11-oxo derivative 4 and 12-oxo derivative 6. The reaction of lupane triterpenoid 2b with reagent system A gave only oxidative rearrangement compounds, (20R)-aldehyde 8 and (20S)-aldehyde 9 were epimeric isomers.

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Accession: 010885465

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PMID: 10705487

DOI: 10.1248/cpb.48.120



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