Intramolecular cyclization of α-bisabolol promoted by arylthionyl iodide under microwave irradiation

The α-bisabolol is a natural product abundant in the Cerrado/Brazil. It presents important biological properties and several applications in medicinal chemistry, such as antifungal, and anti-inflammatory. In organic synthesis bisabolol can be used as an electrophile in cyclization reactions leading to the construction of heterocycles - constituents of several biologically active natural products - in a stereoselective manner. In this sense, we have developed an alternative methodology to synthesize cyclic arylselenoethers through reaction between diphenyl disulfide and (-)-α-bisabolol under microwave irradiation. The cyclization was promoted by diphenyl disulfide through electrophilic addition on vinyl carbon of (-)-α-bisabolol. In summary, an efficient methodology for the synthesis of arylsulfideethers has been described. The main advantage of this method is the utilization of microwave irradiation, under mild reaction conditions and short reaction time. Thescope of the reaction is still under evaluation and we should report briefly the results using derivatives of diaryldisulfide and diaryldiselenide.