A Total Synthesis of Paeoveitol

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 react...

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Bibliographic Details
Published in:Organic letters 2016-08, Vol.18 (15), p.3698-3701
Main Authors: Xu, Lun, Liu, Fengyi, Xu, Li-Wen, Gao, Ziwei, Zhao, Yu-Ming
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01736