Generation of Fused Seven-Membered Polycyclic Systems via Ring Expansion and Application to the Total Synthesis of Sesquiterpenoids
Zhimin Xing, Bowen Fang, Shangwen Luo, Xingang Xie, Xiaolei Wang
Abstract
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.
Topics & Concepts
CycloheptaneRing (chemistry)ChemistryDecaneStereochemistryBicyclic moleculeCombinatorial chemistryOrganic chemistrySynthetic Organic Chemistry MethodsChemical synthesis and alkaloidsAdvanced Synthetic Organic Chemistry