Total synthesis of haminol A: an analysis of vinylpyridine metathesis reactivity |
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| Authors: | Jennifer M StorvickEvgenia Ankoudinova Brianne R KingHeather Van Epps Gregory W O’Neil |
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| Institution: | a Department of Chemistry, Western Washington University, Bellingham, WA 98225-9170, United States
b Department of Biology, Western Washington University, Bellingham, WA 98225-9160, United States |
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| Abstract: | The total synthesis of haminol A has been completed featuring a masked-alkene metathesis reaction followed by bis-acyloxysulfone elimination to install the 1,3,8-triene subunit. During the course of our synthesis, the metathesis reactivity of 3-vinylpyridine was evaluated and our data suggest the rapid formation of a ruthenium pyridylalkylidene that no longer participates in productive metathesis. A chemotaxis assay using Caenorhabditis elegans demonstrated that haminol A produced an avoidance response from this organism. |
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| Keywords: | Olefin metathesis β-Acyloxysulfones Pyridine metathesis Natural products Alarm pheromones |
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