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Formal Synthesis of (±)-Pentalenolactone A Methyl Ester
Guang-Hao Niu1, Pin-Heng Liu1, Wei-Chun Hung1
1Department of Chemistry , Chung Yuan Christian University , Chung-Li, Taoyuan City 32023 , Taiwan.
Abstract:
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).
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