Enantio- and Diastereoselective Synthesis of Tricyclic Lactones Bearing Three Quaternary Stereocenters
Yasuaki Furuya1, Kazunobu Igawa2, Seiji Shirakawa1
1Institute of Integrated Science and Technology, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan.
Abstract:
An efficient method for the enantio- and diastereoselective synthesis of tricyclic γ-butyrolactones bearing three quaternary stereocenters has been developed through transformations of achiral alkenoic acid substrates. The target optically active tricyclic lactones were obtained as single diastereomers with good enantioselectivities through a sequence of catalytic asymmetric bromolactonization, azidation, and subsequent 1,3-dipolar cycloaddition. The origin of the complete diastereoselectivity observed in the formation of the tricyclic γ-butyrolactone products was elucidated in this study.
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