NITROUS ACID DEAMINATION OF 19-NORABIETA-8,11,13-TRIEN-4-AMINE

The conversion of abieta-8,11,13-trien-19-oic acid I (R = COOH) to 19-norabieta-8,11,13-trien-4-amine I (R = NH2) has been achieved in high yield. Nitrous acid deamination of the tertiary amine I (R = NH2) gave a mixture of alkenes IV, V, VI together with a tertiary acetate I (R = OAc) and a tertiary alcohol I (R = OH). 18,19-Dinorabieta-8,11,13-trien-4-one II, a valuable intemediate in steroidal synthesis, was formed by oxidation of the alkene mixture with osmium tetroxide-sodium metaperiodate. The deamination products are discussed in the light of those products obtained from the nitrous acid deamination of other alicyclic systems. © 1969.