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Biomimetic Total Synthesis of (±)-Lappaceolides A and B
Rajanish R Pallerla1, Jenna Hakola1, Leevi Härkönen1
1Department of Chemistry and Materials Science, Aalto University, Kemistintie 1, FI-02150 Espoo, Finland.
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The first total synthesis of lappaceolides A and B is achieved in two steps by using a biomimetic vinylogous-Michael-oxa-Michael domino reaction. The domino reaction proceeds with Cs2CO3 in 1,2-DCE at elevated temperatures and requires careful kinetic control. The total synthesis provides further proof of the biosynthetic hypothesis of lappaceolides being dimers of the natural product siphonodin.
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