title: A Total Synthesis of Paeoveitol.
abstract: 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.
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering Shaanxi Normal University , 620 West Chang'an Ave, Xi'an, 710119, China.
authors.forename: Lun
authors.initials: L
authors.lastname: Xu
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering Shaanxi Normal University , 620 West Chang'an Ave, Xi'an, 710119, China.
authors.forename: Fengyi
authors.initials: F
authors.lastname: Liu
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering Shaanxi Normal University , 620 West Chang'an Ave, Xi'an, 710119, China.
authors.forename: Li-Wen
authors.initials: LW
authors.lastname: Xu
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering Shaanxi Normal University , 620 West Chang'an Ave, Xi'an, 710119, China.
authors.forename: Ziwei
authors.initials: Z
authors.lastname: Gao
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering Shaanxi Normal University , 620 West Chang'an Ave, Xi'an, 710119, China.
authors.forename: Yu-Ming
authors.initials: YM
authors.lastname: Zhao