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

Article abstract of DOI:10.1016/S0040-4039(98)02493-9

The structure of cepaciamide A was revised to be (3R,3'S,2'S,11'S,12'R)- 3-[3'-(2'hydroxy-11', 12'-methylencoetadecanoyloxy)hexadecamido]-2- piperidinone with respect to the absolute configuration of the C₃- and C₂- positions and the position of the cyclopropane ring by using synthetic methods. The structure of cepaciamide B was also determined to be (3R,3'S,2'S, 11'Z)'3'[3'(2'-hydroxy-11_-octadecenoyloxy)hexadecamido]-2- piperidinone.