Reactions of the Lythraceae alkaloids. Regio and stereoselective methoxylations and hydroxylations of lythrine

Mercuric acetate assisted methoxylations and hydroxylations of lythrine resulted in a regio and stereoselective introduction of the substituent at the benzylic position with S-stereochemistry. The compounds obtained are thus epimeric at C13 with the naturally hydroxylated alkaloid lythridine and its derivatives. The implications of the results in planning the total synthesis of lythrine is discussed.