化学
鞣花单宁
酰化
产量(工程)
立体化学
化学合成
限制
二聚体
组合化学
有机化学
生物化学
催化作用
体外
机械工程
工程类
多酚
材料科学
冶金
抗氧化剂
作者
Ken S. Feldman,Michael D. Lawlor,Kiran Sahasrabudhe
摘要
The total synthesis of the dimeric ellagitannin coriariin A is reported. The key reaction to access the dimeric framework was realized early in the synthesis pathway via a bis acylation reaction of a dehydrodigalloyl diacid with 2 equiv of a glucopyranose trichloroacetimidate. The glucose rings were subsequently functionalized, culminating in a double oxidative cyclization to form stereoselectively both (S)-HHDP ester units. This bis acylation strategy was also employed to prepare a gallotannin analogue of coriariin A whose earlier synthesis by orthoquinone dimerization was plagued by yield-limiting side reactions.
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