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11-Step Total Synthesis of Pallambins C and D

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journal contribution
posted on 2016-06-10, 13:18 authored by Luisruben P. Martinez, Shigenobu Umemiya, Sarah E. Wengryniuk, Phil S. Baran
The 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.

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