Significant acceleration of 6π-azaelectrocyclization resulting from a remarkable substituent effect and formal synthesis of the ocular age pigment A2-E by a new …

…, H Mori, M Yamamoto, S Katsumura

Index: Tanaka; Mori; Yamamoto; Katsumura Journal of Organic Chemistry, 2001 , vol. 66, # 9 p. 3099 - 3110

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Citation Number: 126

Abstract

The remarkable acceleration of 6π-azaelectrocyclization due to the combination of the C4- carbonyl and the C6-alkenyl or phenyl substituents in 1-azatrienes was found. This observation was rationalized by considering the remarkable orbital interaction between the HOMO and LUMO of 1-azatrienes, which were obtained by molecular orbital calculations. The formal synthesis of the unusual retinal metabolite, A2-E, was achieved by two types of ...