4.6 Article

Synthesis of Lignans Based on a Borate-mediated One-pot Sequential Suzuki-Miyaura Coupling of Cyclic Boranes

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 36, Pages 9422-9428

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100804

Keywords

Borate; Hydroboration; Lignans; Suzuki-Miyaura Coupling; Total Synthesis

Funding

  1. JSPS KAKENHI [JP18H04390]

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In this study, a borate-mediated one-pot sequential Suzuki-Miyaura coupling method was successfully used to synthesize various lignan compounds, achieving the synthesis of naturally occurring lignans through asymmetric cyclic hydroboration and a series of reaction steps.
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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