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Updated: Feb 8, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Syntheses of Polycyclic Tetrahydrofurans by Cascade Reactions Consisting of Five-Membered Ring Selective Prins
Yuki Sakata1, Eiko Yasui1, Kazuhiko Takatori2
1Department of Applied Chemistry , Kogakuin University , Nakano 2665-1 , Hachioji, Tokyo 192-0015 , Japan.
Abstract:
A novel cascade reaction consisting of a five-membered ring selective Prins cyclization and a subsequent Friedel-Crafts cyclization is reported. Treatment of homocinnamyl alcohols and aromatic aldehydes with BF3·OEt2 in CH2Cl2 afforded hydrocyclopentafurans. Also hydrocyclopentafurans underwent the same cascade reaction after its furan ring cleavage upon treatment with BF3·OEt2 at room temperature. Various combinations of hydropentafurans and aromatic aldehydes or indole aldehydes permitted divergent synthesis of diquinane-furans stuck in aromatic rings.
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