Sakata Yuki, Yasui Eiko, Takatori Kazuhiko, Suzuki Yuji, Mizukami Megumi, Nagumo Shinji
Department of Applied Chemistry , Kogakuin University , Nakano 2665-1 , Hachioji, Tokyo 192-0015 , Japan.
Department of Synthetic Organic Chemistry , Meiji Pharmaceutical University , Noshio 2-522-1 , Kiyose, Tokyo 204-8588 , Japan.
J Org Chem. 2018 Aug 17;83(16):9103-9118. doi: 10.1021/acs.joc.8b01195. Epub 2018 Jul 24.
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 BF·OEt in CHCl afforded hydrocyclopentafurans. Also hydrocyclopentafurans underwent the same cascade reaction after its furan ring cleavage upon treatment with BF·OEt at room temperature. Various combinations of hydropentafurans and aromatic aldehydes or indole aldehydes permitted divergent synthesis of diquinane-furans stuck in aromatic rings.
报道了一种由五元环选择性普林斯环化和随后的傅克环化组成的新型级联反应。在二氯甲烷中用三氟化硼乙醚处理高肉桂醇和芳香醛可得到氢化环戊并呋喃。此外，氢化环戊并呋喃在室温下用三氟化硼乙醚处理使其呋喃环裂解后也能发生相同的级联反应。氢化环戊并呋喃与芳香醛或吲哚醛的各种组合能够实现被困在芳香环中的二喹烷 - 呋喃的发散合成。
