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A short, highly efficient synthesis of advanced intermediates to reserpine 1 has been developed starting from enamide 8 . The enamide underwent photocyclization reaction using high pressure mercury lamp to afford the lactam 9 in excellent yield. Then lactam was reduced to the required amine 10 , which upon acidic hydrolysis gave the nonconjugate ketone product 11 , followed by reaction with sodium hydroxide resulted the desired conjugate ketone 12 . Epoxidation, and then ring opening of the epoxide 13 with methanol yielded the desired product 14 , which is key intermediate to the total synthesis of (±)-reserpine.

european journal of chemistry

Studies towards the synthesis of (±)-reserpine: Photocyclization mediated a novel and efficient synthesis of 11,18-dimethoxy-(20α)-18,19-didehydro-yohimban-17-one