Abstract
The carbinolamine 2 is oxidized with oxygen to give the peroxide 6 whose structure is established on the basis of the spectral properties and the structure of the hexahydro-chelerythrine 7 obtained on the sodium borohydride reduction. Formation pathway of the peroxide 6 is examined. Treatment of the peroxide 6 with 2, 3-dichloro-5, 6-dicyano-benzoquinone (DDQ) affords the keto amide 10, two nitriles 11 and 12, and keto aldehyde 13. Structures for these compounds are mainly proved by the spectral data. Further, it is examined that these compounds are probably formed by oxidation and reduction of the peroxide 6 with DDQ and 2, 3-dichloro-5, 6-dicyanohydroquinone resulted from DDQ during reaction.
