Total Synthesis of Cinnamodial-Based Dimer (-)-Capsicodendrin

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We describe the first total synthesis of cinnamodial-based dimer (−)-capsicodendrin. First, we developed a 12-step synthetic route to access (−)-cinnamodial from 1-vinyl-2,6,6-trimethylcyclohexene. We then showed that (−)-cinnamodial can selectively dimerize to (−)-capsicodendrin under kinetically controlled basic conditions. Our observations regarding a facile conversion of (−)-capsicodendrin back to (−)-cinnamodial hint at the possibility that (−)-capsicodendrin is a chemical reservoir of insecticidal (−)-cinnamodial and Cinnamosma genus plants release it upon environmental stresses.
Publisher
AMER CHEMICAL SOC
Issue Date
2020-06
Language
English
Article Type
Article
Citation

JOURNAL OF ORGANIC CHEMISTRY, v.85, no.11, pp.7576 - 7582

ISSN
0022-3263
DOI
10.1021/acs.joc.0c00740
URI
http://hdl.handle.net/10203/274582
Appears in Collection
CH-Journal Papers(저널논문)
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