Tetrahedron

Addition of silyloxydienes to 2, 6-dibromo-1, 4-benzoquinone: an approach to highly oxygenated bromonaphthoquinones for the synthesis of thysanone

D Barker, MA Brimble, P Do, P Turner

文献索引：Barker, David; Brimble, Margaret A.; Do, Peter; Turner, Peter Tetrahedron, 2003 , vol. 59, # 14 p. 2441 - 2449

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被引用次数: 30

摘要

The synthesis of tetraoxygenated bromonaphthoquinones 6a, 6b, 6c, 6d, key intermediates for a synthesis of the 3C protease inhibitor, thysanone, were investigated. Addition of 1- methoxy-1, 3-bis (trimethylsilyloxy)-1, 3-butadiene 8 to 2, 6-dibromo-1, 4-benzoquinone 10 in benzene afforded a mixture of naphthoquinone 6a, arising from Diels–Alder addition followed by aromatisation, and Michael adduct 12. The Michael adduct 12 predominated ...