Lee Y, Silverman R B
Department of Chemistry, Northwestern University, Evanston, Illinois 60208-3113, USA.
Org Lett. 2000 Nov 16;2(23):3743-6. doi: 10.1021/ol0002830.
A 10-step solid-phase synthesis of the cytotoxic depsipeptide sansalvamide A (1) has been accomplished in an overall yield of 67% with >95% purity employing polymer-bound phenylalanine building block 2. Both the N- and C-termini of 2 are extended followed by on-resin head-to-tail macrocyclization of the linear peptide in a high yield. This should be a general stategy for the synthesis of diverse libraries of cyclic peptides and depsipeptides that contain exclusively phenylalanine and other hydrophobic side chains.
