Syntheses of Polycyclic Tetrahydrofurans by Cascade Reactions Consisting of Five-Membered Ring Selective Prins Cyclization and Friedel-Crafts Cyclization

被引：25

作者：

Sakata, Yuki ^{[1
]}

Yasui, Eiko ^{[1
]}

Takatori, Kazuhiko ^{[2
]}

Suzuki, Yuji ^{[1
,3
]}

Mizukami, Megumi ^{[3
]}

Nagumo, Shinji ^{[1
]}

机构：

[1] Kogakuin Univ, Dept Appl Chem, Nakano 2665-1, Hachioji, Tokyo 1920015, Japan

[2] Meiji Pharmaceut Univ, Dept Synthet Organ Chem, Noshio 2-522-1, Tokyo 2048588, Japan

[3] Hokkaido Univ Sci, Fac Pharmaceut Sci, Dept Med Chem, Maeda 15-4-1, Sapporo, Hokkaido 0068585, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 16期

关键词：

METHOXYCARBONYL OXYCARBENIUM IONS; STEREOSELECTIVE-SYNTHESIS; PI-CYCLIZATIONS; ONE-POT; TETRAHYDROPYRANS; DERIVATIVES; ROSEOPHILIN;

D O I：

10.1021/acs.joc.8b01195

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 center dot OEt2 in CH2Cl2 afforded hydrocyclopentafurans. Also hydrocyclopentafurans underwent the same cascade reaction after its furan ring cleavage upon treatment with BF3 center dot OEt2 at room temperature. Various combinations of hydropentafurans and aromatic aldehydes or indole aldehydes permitted divergent synthesis of diquinane-furans stuck in aromatic rings.

引用

页码：9103 / 9118

页数：16

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