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11-Step Total Synthesis of Pallambins C and D.

ABSTRACT: 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.

SUBMITTER: Martinez LP

PROVIDER: S-EPMC4919752 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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11-Step Total Synthesis of Pallambins C and D.

Martinez Luisruben P LP Umemiya Shigenobu S Wengryniuk Sarah E SE Baran Phil S PS

Journal of the American Chemical Society 20160610 24

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 difunctio ...[more]

PMID: 27284962

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