A strained 14-membered cyclopeptide was prepared from the Garner aldeh
yde derived from D-serine. The key steps in the synthesis were the con
struction of the alkyl-aryl ether linkage via an SNAr reaction involvi
ng 4-fluorobenzonitrile and the macrolactamization using a modificatio
n of the Schmidt protocol involving an activated pentafluorophenyl est
er. (C) 1998 Elsevier Science Ltd. All rights reserved.