Biomimetic Total Synthesis of (±)-Lappaceolides A and B
Rajanish R. Pallerla, Jenna Hakola, Leevi Härkönen, Juha H. Siitonen
TL;DR
Scientists synthesized lappaceolides A and B in two steps using a biomimetic reaction, supporting their origin from a natural compound.
Contribution
A novel two-step total synthesis of lappaceolides A and B using a biomimetic domino reaction.
Findings
The synthesis used a vinylogous-Michael–oxa-Michael domino reaction with Cs2CO3 in 1,2-DCE.
The reaction required elevated temperatures and precise kinetic control.
The synthesis supports the hypothesis that lappaceolides are dimers of siphonodin.
Abstract
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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Taxonomy
TopicsTraditional and Medicinal Uses of Annonaceae · Marine Sponges and Natural Products · Synthetic Organic Chemistry Methods