Journal
TETRAHEDRON LETTERS
Volume 52, Issue 44, Pages 5858-5861Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.08.153
Keywords
Olefin metathesis; beta-Acyloxysulfones; Pyridine metathesis; Natural products; Alarm pheromones
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Funding
- American Chemical Society [49499-UNI]
- Western Washington University
- M.J. Murdock Charitable Trust
- Research Corporation departmental development grant
- Washington NASA Space Grant Consortium
- NIH National Center for Research Resources (NCRR)
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The total 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. (C) 2011 Elsevier Ltd. All rights reserved.
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