キラルLewis酸テンプレートを用いる不斉Diels-Alder反応と天然物合成への応用

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  • Chiral Lewis Acid-template Diels-Alder Reaction and the Application of Natural Product Synthesis

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<p>The tethered Diels-Alder reaction is one of the most powerful and versatile methods for formation of functionalized cyclohexene derivatives with high regio- and stereoselectivity. Many advantages of the intramolecular Diels-Alder reaction have been extended to the intermolecular counterpart by linking the diene to the dienophile with a temporary tether. This account describes some highlights of template-mediated Diels-Alder reactions, together with our asymmetric Diels-Alder reaction of 2,4-dienols and methyl acrylate utilizing a bimetallic Lewis acid template derived from (R)-5,5’,6,6’,7,8,8’-octahydro-1,1’-bi-2-naphthol. The bimetallic Lewis acid-template Diels-Alder reaction is feasible to hetero-Diels-Alder reaction of 4-siloxy-2,4-penta-dienols and aldehydes to provide substituted dihydropyrans with good enantioselectivities. The synthetic application for biologically active compounds is also demonstrated.</p>

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