Tetrahedron

Synthese industrielle en serie ellipticine. I: Elaboration d'une nouvelle voie d'accès aux 6H-pyrido [4, 3: b] carbazoles et analogues: A. Synthèse et étude des …

JR Dormoy, A Heymes

Index: Dormoy, Jean-Robert; Heymes, Alain Tetrahedron, 1993 , vol. 49, # 14 p. 2885 - 2914

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Citation Number: 34

Abstract

Total synthesis of modified ellipticines 1c and 1f is described from 2-chloronicotinic acid and respectively 5-methoxy-indole and 5-azaindole in 11 to 13 steps with overall yields of 11% and 18%. A new route to 5-azaindole has also been developed. The synthetic strategy calls for frequent use of homo-and hetero aromatic metallation reactions necessiting resolution of problems associated with the presence of the pyridine ring. With respect to the numerous ...