The Synthesis of an Aziridinyl Analogue of Unit A of Cryptophycin-1

A novel analogue of unit A of cryptophycin-1 was prepared starting from commercial trans-cinnamaldehyde. The modifications introduced into the new structure related to the replacement of the epoxide with an aziridine moiety, and the inclusion of the 1,3-enone moiety into an aromatic ester frame through the synthesis of a key aromatic ketone. Asymmetry was induced during the later steps of the synthetic pathway. The optical purity of compounds was monitored by chiral HPLC and polarimetric measurements.