11-Step Total Synthesis of Pallambins C and D

作者:Martinez Luisruben P; Umemiya Shigenobu; Wengryniuk Sarah E; Baran Phil S
来源:Journal of the American Chemical Society, 2016, 138(24): 7536-7539.
DOI:10.1021/jacs.6b04816

摘要

The structurally intriguing terpenes pallam-bins 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.

  • 出版日期2016-6-22