ja6b04816_si_001.pdf (3.68 MB)
11-Step Total Synthesis of Pallambins C and D
journal contribution
posted on 2016-06-10, 13:18 authored by Luisruben
P. Martinez, Shigenobu Umemiya, Sarah E. Wengryniuk, Phil S. BaranThe
structurally intriguing terpenes pallambins C and D have been
assembled in only 11 steps from a cheap commodity chemical: furfuryl
alcohol. This synthesis, which features a redox-economic approach
free of protecting-group manipulations, assembles all four-ring systems
via a sequential cyclization strategy. Of these four-ring constructing
operations, two are classical (Robinson annulation and Mukaiyama aldol)
and two are newly devised. During the course of this work a method
for the difunctionalization of enol ethers was developed, and the
scope of this transformation was explored.