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Synthesis of Lignans Based on a Borate-mediated One-pot Sequential Suzuki-Miyaura Coupling of Cyclic Boranes
1Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1-H101 Ookayama, Meguro, Tokyo, 152-8552, Japan.
Abstract:
Lignans are a group of polyphenolic phytochemicals that possess a large spectrum of chemical structures and biological activities. Here the syntheses of lignans - anwulignan, burseran, dehydroxycubebin, ruburisandrin B, and sesamin - are achieved based on a borate-mediated one-pot sequential Suzuki-Miyaura coupling of cis- and trans-fused bicyclic boranes, which were prepared by diastereoselective cyclic hydroboration of exo-cyclic diene with cyclopentyl- and thexylboranes, respectively. A one-pot sequential Suzuki-Miyaura coupling of each cyclic borate with various aryl bromides initiated by activation of the cyclic borane with the carbon nucleophile provided 2,3-dibenzylbutane derivatives with different aromatic substituents. Finally, the syntheses of naturally occurring lignans were accomplished in several steps from the products of Suzuki-Miyaura coupling.
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