有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
ビアリールカップリング反応を利用する天然物合成
阿部 仁
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ジャーナル 認証あり

2017 年 75 巻 8 号 p. 850-863

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The intramolecular aryl-aryl coupling reaction of phenyl benzoate derivatives is a convenient method for construction of a 6H-dibenzo [b,d] pyran-6-one skeleton which is frequently found in natural products. Palladium reagents are used for the C-C bond formation between two aromatic rings. This review article describes that this technique is effective for the syntheses of several natural products possessing a highly oxygenated 6H-dibenzo [b,d] pyran-6-one core. The regioselectivity in the reaction is also discussed with some transition state illustrations. For further application, asymmetric construction of the biphenyl moiety is presented using the dynamic kinetic optical resolution method.

In the latter part, the biphenyl synthesis and the diphenyl ether synthesis under the Ullmann conditions are described toward the total synthesis of ellagitannins. The syntheses of several important part structures of ellagitannins are illustrated using the Ullmann reactions. Finally, one example of the total synthesis of ellagitannin is demonstrated.

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