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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 ??-?? stacking interaction that govern selectivity in this process.

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Xu, L.; Liu, F.; Xu, L.-W.; Gao, Z.; Zhao, Y.-M. Org. Lett. 2016, ASAPContributed by Steven BacharachReposted from Computational Organic Chemistry with permissionXu, Liu, Xu, Gao, and Zhao report a very efficient synthesis of paeoveitol 1 by the [4+2]-cycloaddition...
Xu, Liu, Xu, Gao, and Zhao report a very efficient synthesis of paeoveitol 1 by the [4+2]-cycloaddition of paeveitol D 2 with the o-quinone methide 3.1 What is interesting here is the selectivity of this reaction. In principle the cyloadditon can give four...