Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 24, Pages 7536-7539Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b04816
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- NSF GRFP
- JSPS
- NIH [GM-097444]
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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.
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