A Total Synthesis of Paeoveitol

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• 作者：Lun Xu ; Fengyi Liu ; Li-Wen Xu ; Ziwei Gao ; Yu-Ming Zhao
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：18
• 期：15
• 页码：3698-3701
• 全文大小：377K
• 年卷期：0
• ISSN：1523-7052

文摘

A four-step total synthesis of paeoveitol (1), a recently disclosed norditerpene natural product from Paeonia vetchii, is reported. This highly concise synthetic route was guided by biosynthetic considerations and enabled by an unusual intermolecular ortho-quinone methide [4 + 2]-cycloaddition reaction, which proceeded with excellent regio- and diastereoselectivity. Density functional theory (DFT) calculations point to a crucial intermolecular hydrogen bond and π–π stacking interaction that govern selectivity in this process.