Journal of the American Chemical Society

A general synthesis of the troponoid system based on solvolysis of 1, 4-dihydrobenzyl tosylates

OL Chapman, P Fitton

文献索引：Chapman,O.L.; Fitton,P. Journal of the American Chemical Society, 1963 , vol. 85, p. 41 - 47

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被引用次数: 38

摘要

Birch reduction of 3, 4, 5-trimethoxybenzoic acid gives 3, 5-dimethoxy-1, 4-dihydrobenzoic acid. Lithium alumi-num hydride reduction of the dihydroacid followed by tosylation and solvolysis of the tosylate in pyridine gives a mixture of 1, 3-dimethoxycycloheptatrienes which on bromine oxidation gives 8-tropolone in 28% average overall yield. This method has been applied to the synthesis of a-tropolone from 2, 3-dimethoxybenzoic acid, y- ...