Journal
TETRAHEDRON LETTERS
Volume 57, Issue 2, Pages 237-238Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.12.043
Keywords
Junionone; Dimethylketene; Cyclobutanone; Huang-Minlon reduction; Wacker-Tsuji oxidation
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Funding
- National Institutes of Health [SC1 GM082340]
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Junionone is the first monocyclic cyclobutane monoterpenoid isolated from a plant. Of the existing four syntheses of this compound, none employs a ketene cycloaddition to construct the four-membered ring. Herein, we report the first total synthesis of junionone that features a ketene cycloaddition for the synthesis of this compound, starting from the commercially available 1,5-hexadiene. (C) 2015 Elsevier Ltd. All rights reserved.
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