Tetrahedron

Synthesis of a regioisomeric analogue of the 3C-protease inhibitor thysanone via a Hauser annulation strategy

MA Brimble, SI Houghton, PD Woodgate

文献索引：Brimble, Margaret A.; Houghton, Scott I.; Woodgate, Paul D. Tetrahedron, 2007 , vol. 63, # 4 p. 880 - 887

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被引用次数: 20

摘要

Hauser annulation of 3-cyano-5, 7-dimethoxy-(3H)-isobenzofuran-1-one 4 with ethyl acrylate as a method to access activated naphthoquinone 3, a key intermediate for the synthesis of thysanone 1, proved unreliable. In contrast to this, Hauser annulation of regioisomeric 3-cyano-4, 6-dimethoxy-(3H)-isobenzofuran-1-one 13 with ethyl acrylate proceeded readily affording ethyl 5, 7-dimethoxy-1, 4-naphthoquinone 12, after oxidation ...