Chemistry Letters, Vol.29, No.9, 1104-1105, 2000
Synthesis of polyamine alkaloids by the condensation of a chiral beta-lactam with a cyclic imino ether. (S)-dihydroperiphylline and its derivatives
The synthesis of 13-membered polyamine alkaloid, (S)-dihydroperiphylline, was achieved by the condensation of a chiral beta-lactam, (S)-4-phenyl-2-azetidinone, with a cyclic imino ether of a 9-membered lactam, followed by reductive ring expansion. Both of these reactions proceeded with retention of configuration around the chiral center to give the optical pure 13-membered alkaloids.