Tetrahedron

Directed ortho metallation of tertiary aromatic amides: A new n-heteroring annelation method and synthesis of phenanthro-quinolizidine and-indolizidine alkaloids

M Iwao, KK Mahalanabis, M Watanabe, SO De Silva…

文献索引：Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; Silva, S. O. De; Snieckus, V. Tetrahedron, 1983 , vol. 39, # 12 p. 1955 - 1962

全文：HTML全文

被引用次数: 44

摘要

The synthesis of phenanthro-quinolizidine and-indolizidine alkaloids, cryptopleurine (8) and antofine (9) via directed ortho metallation of the common phenanthrene (1) are described (Scheme 2). The utility of this strategy as a new N-heteroring annelation method (Scheme 1) is illustrated by the preparation of other aromatic ring-fused quinolizidine (12, 15) and indolizidine (18, 21) systems. A Mg for Li transmetallation, crucial for the synthesis of 13 ...