Generation of Fused Seven-Membered Polycyclic Systems via Ring Expansion and Application to the Total Synthesis of Sesquiterpenoids

Generation of Fused Seven-Membered Polycyclic Systems via Ring Expansion and Application to the Total Synthesis of Sesquiterpenoids

Seven-membered polycyclic architectures, widely present in natural products and molecular drugs, are challenging synthetic targets. However, methods for synthesizing fused medium-sized bicyclo­[m.n.0] ring systems, including the benzo-cycloheptane systems, are still urgent. Herein we describe a base...

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Veröffentlicht in:Organic letters 2022-06, Vol.24 (22), p.4034-4039
Hauptverfasser: Xing, Zhimin, Fang, Bowen, Luo, Shangwen, Xie, Xingang, Wang, Xiaolei
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container_issue 22
container_start_page 4034
container_title Organic letters
container_volume 24
creator Xing, Zhimin
Fang, Bowen
Luo, Shangwen
Xie, Xingang
Wang, Xiaolei
description Seven-membered polycyclic architectures, widely present in natural products and molecular drugs, are challenging synthetic targets. However, methods for synthesizing fused medium-sized bicyclo­[m.n.0] ring systems, including the benzo-cycloheptane systems, are still urgent. Herein we describe a base-induced ring expansion as a general strategy to construct a wide range of fused seven-membered ring systems. The application of this method was demonstrated by the efficient total syntheses of two sesquiterpenoids, plecarpenene and plecarpenone, both bearing a fused bicyclo[5.3.0]­decane skeleton.
doi_str_mv 10.1021/acs.orglett.2c01401
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title Generation of Fused Seven-Membered Polycyclic Systems via Ring Expansion and Application to the Total Synthesis of Sesquiterpenoids
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