Rauwolfia Alkaloids. XLV. Preparation and Transformations of the Ketone Derived from Methyl Reserpate

Dimethyl Sulfoxide Oxidations

“…The following discussion will consider oxidations proceeding by pathway B, i.e., formation of the dimethylalkoxysulfonium salt III by direct nucleophilic displacement of a leaving group by DMSO. Applications of this technique to -halo esters (Br, Cl, I) or acids (34), phenacyl halides (48,59), benzyl halides (49, 68), primary sulfonates (49, 60, 68), primary iodides (37), and a limited number of secondary halides (35,67,92) and secondary tosylates (36,42,83) have been successful in a preparative sense. Oxidation never proceeds past the carbonyl, and other functional groups remain generally inert.…”