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11-Step Total Synthesis of Pallambins C and D
Martinez, LP Umemiya, S Wengryniuk, SE Baran, PS
Martinez, LP
Umemiya, S
Wengryniuk, SE
Baran, PS
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Journal Article
Date
2016-06-22
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10.1021/jacs.6b04816
Abstract
© 2016 American Chemical Society. 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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Journal of the American Chemical Society
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