Total synthesis of malyngamide M and isomalyngamide M

The stereoselective synthesis of malyngamide M (1) was accomplished in nine steps from o-cresol in 12% overall yield. The key steps involved the Wittig reaction of an α-NHBoc aryl ketone 4 for the introduction of vinyl chloride functionality, an amidation of lyngbic acid 3 with a secondary amine 2 for the framework of target molecule, and an isomerization of a (Z)-vinyl chloride to the (E)-configuration using benzophenone as a photosensitizer. The isomalyngamide M (Z-1) was also synthesized.