Beilstein J. Org. Chem.2012,8, 164–169, doi:10.3762/bjoc.8.17
/bjoc.8.17 Abstract A new, straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding δ-hydroxy-γ-lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a
: bismuth(III) triflate; δ-hydroxy-γ-lactones; MMPP; oleanolic acid; triterpenoid; Findings
The molecular diversity that arises from research into natural products represents a valuable tool for driving drug discovery and development [1][2]. In this context, pentacyclic triterpenoids are currently regarded
of ring C, a strategy known to increase the anti-inflammatory and cytotoxic activities of oleanolic acid (OA) derivatives [19][21][22].
Oleanolic δ-hydroxy-γ-lactones can be obtained from Δ12-oleananes by oxidative 28,13β-lactonization. This reaction was performed under photochemical irradiation [23
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Graphical Abstract
Figure 1:
ORTEP diagram of compound 4 (50% probability level, H atoms of arbitrary sizes). The asymmetric uni...