Australian Journal of Chemistry

Convergent Routes to the [1, 3] Dioxolo [4, 5-j] phenanthridin-6 (5H)-one and 2, 3, 4, 4a-Tetrahydro [1, 3] dioxolo [4, 5-j] phenanthridin-6 (5H)-one Nuclei. Application …

MG Banwell, CJ Cowden

文献索引：Banwell, Martin G.; Cowden, Cameron J. Australian Journal of Chemistry, 1994 , vol. 47, # 12 p. 2235 - 2254

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被引用次数: 34

摘要

Abstract Convergent routes to the title nuclei,(1) and (6), have been developed. Thus, Suzuki coupling of boronic acid (8) with aryl bromide (9) gave the biarylylcarbamate (7) which, on treatment with phosphorus oxychloride (POCl 3), underwent Bischler-Napieralski cyclization to give, after acid hydrolysis, the Amaryllidaceae alkaloid crinasiadine (1). The cyclization reaction proceeds via an intermediate chlorophenanthridine (11) which can be isolated ...