Formal Synthesis of (±)-Pentalenolactone A Methyl Ester

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 fo...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-08, Vol.84 (16), p.10172-10182
Main Authors: Niu, Guang-Hao, Liu, Pin-Heng, Hung, Wei-Chun, Tseng, Ping-Yao, Chuang, Gary Jing
Format: Article
Language:English
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Summary: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).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01349