Synthetic studies of 14-membered cyclopeptide alkaloids

Article abstract of DOI:10.1016/S0040-4039(98)01589-5

A strained 14-membered cyclopeptide was prepared from the Garner aldehyde derived from D-serine. The key steps in the synthesis were the construction of the alkyl-aryl ether linkage via an S(N)Ar reaction involving 4-fluorobenzonitrile and the macrolactamization using a modification of the Schmidt protocol involving an activated pentafluorophenyl ester.