Synthesis of (±)tetrahydromyricoidine

Article abstract of DOI:10.1016/S0040-4020(01)80423-3

A total synthesis of the spermidine alkaloid (±)-tetrahydromyricoidine (6) was achieved by using two ring enlargement reactions. The difficulties experienced in the second ring enlargement step, a transamidation reaction with a medium ring sized lactam bearing two bulky groups are discussed. These were overcome by altering the reaction sequence and the transamidation reaction was successfully carried out by at first deprotection of the Boc function. spermidine alkaloids; (±)-tetrahydromyricoidine; ring enlargement.