Studies toward the Synthesis of Colletotrichamide A: Construction of the C19–C30 Segment of the Molecule

Abstract

AbstractA synthesis of the C19–C30 segment of the neuroprotective natural product colletotrichamide A has been achieved by performing a Sonogashira coupling of two advanced intermediate fragments: a vinyl iodide and an alkyne. A Maruoka–Keck allylation, an Evans syn-aldol reaction, and Takai olefinations served as the key steps in the synthesis of the vinyl iodide intermediate, whereas glycosidation and Ohira–Bestmann reactions were used as the pivotal steps for accessing the advanced alkyne intermediate.