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Formal Synthesis of (±)-Pentalenolactone A Methyl Ester

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journal contribution
posted on 25.07.2019, 13:08 by Guang-Hao Niu, Pin-Heng Liu, Wei-Chun Hung, Ping-Yao Tseng, Gary Jing Chuang
We report the formal synthesis of (±)-pentalenolactone A methyl ester from simple 2-methoxyphenol. The key features of our route are as follows: a Diels–Alder reaction of masked o-benzoquinone to assemble the functionalized bicyclo[2.2.2]­octenone, a continuous-flow oxa-di-π-methane rearrangement for building the diquinane core (AB ring), and an oxidative cleavage/oxidation sequence for annulation of the δ-lactone (C ring).