De Novo Asymmetric Synthesis of an α-6-Deoxyaltropyranoside as Well as its 2-/3-Deoxy and 2,3-Dideoxy Congeners

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• 作者：Mingde Shan ; Yalan Xing ; George A. O’ ; Doherty
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：August 21, 2009
• 年：2009
• 卷：74
• 期：16
• 页码：5961-5966
• 全文大小：811K
• 年卷期：v.74,no.16(August 21, 2009)
• ISSN：1520-6904

文摘

A highly divergent de novo asymmetric synthesis of benzyl α-6-deoxyaltropyranoside, benzyl α-ascarylopyranoside, benzyl α-amicetopyranoside, and benzyl α-digitoxopyranoside has been achieved via a common pyranone intermediate. The routes rely upon a palladium(0)-catalyzed glycosylation reaction and corresponding post-glycosylation transformations. The control of the absolute and relative stereochemical configuration came from a Noyori reduction of 2-acylfuran and subsequent diastereoselective introduction of other stereogenic centers.