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Synthesis of Lignans Based on a Borate‐mediated One‐pot Sequential Suzuki‐Miyaura Coupling of Cyclic Boranes
Author(s) -
Sato Ko,
Tanaka Hiroshi
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100804
Subject(s) - boranes , chemistry , hydroboration , nucleophile , borane , aryl , organic chemistry , lignan , suzuki reaction , diene , boron , medicinal chemistry , combinatorial chemistry , catalysis , alkyl , natural rubber
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.