Synthesis and structure of 8-hydroxy-6-methoxy-3,7-dimethylisochromane and its analogues

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• 作者：Tsuneo Suzuki ; Kiyoshi Tanemura ; Takaaki Horaguchi and Kimiyoshi Kaneko
• 关键词：Heterocycles ; Mycotoxin ; Isochromane ; Formylation ; Catalytic reduction ; Intramolecular cyclization
• 刊名：Tetrahedron
• 出版年：2006
• 出版时间：10 April 2006
• 年：2006
• 卷：62
• 期：15
• 页码：3739-3751
• 全文大小：641 K

文摘

The title compound 1 was obtained by the reaction of alcohol 18 and triethyl orthoformate catalyzed by aluminum chloride followed by catalytic hydrogenation in good yield. Similarly, compounds 1 and 3 were obtained by intramolecular cyclization of MOM ether 19 with titanium(IV) chloride in moderate yields and isochromanes 1, 3, 26 and 27 by intramolecular cyclization of ether 20 with titanium(IV) chloride in high yields. The structures of compounds 1–3 were elucidated by analysis of spectroscopic data and chemical reactions. The mechanisms on the formation of 1 and 3 are discussed.