Study on fungitoxic 3-amino-2-piperidinone-containing lipids: Revised structure of cepaciamide A and structural determination of its closely related lipid, cepaciamide B

The structure of cepaciamide A was revised to be (3 R ,3′ S ,2″ S ,11″ S ,12″ R )-3-[3′-(2″-hydroxy-11″,12″-methyleneoctadecanoyloxy)hexadecamido]-2-piperidinone with respect to the absolute configuration of the C 3′- and C 2″- positions and the position of the cyclopropane ring by using synthetic methods. The structure of cepaciamide B was also determined to be (3 R ,3′ S ,2″ S ,11″ Z )-3-[3′-(2″-hydroxy-11″-octadecenoyloxy)hexadecamido]-2-piperidinone.