Tetrahedron

Diels-alder cyclization of 2, 8, 10-undecatrienals as a route to 1, 2, 3, 4, 4a, 5, 6, 8a-octahydronaphthalenes

JA Marshall, JE Audia, J Grote, BG Shearer

文献索引：Marshall, James A.; Audia, James E.; Grote, Jonathan; Shearer, Barry G. Tetrahedron, 1986 , vol. 42, # 11 p. 2893 - 2902

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被引用次数: 31

摘要

2, 8, 10-Undecatrienals have been found to undergo facile Diels-Alder cyclization upon treatment with alkylaluminum chlorides in methylene chloride at low temperature. The reaction is highly endo-selective. Protected alcohol substituents at the C-4 and C-7 positions are fully accommodated and TBDMS protected alcohols show a strong axial preference. The methodology has been applied to a hydronaphthalenecarboxylic add of possible use in a ...