Synthesis of dicyclopenta [ef, kl] heptalene (azupyrene). I. Routes to 1, 6, 7, 8, 9, 9a-hexahydro-2H-benzo [c, d] azulen-6-one

AG Anderson Jr, GM Masada…

Index: Anderson,A.G. et al. Journal of Organic Chemistry, 1973 , vol. 38, # 8 p. 1439 - 1444

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Citation Number: 13

Abstract

As the first phase in the synthesis of dicyclopenta [ef, kl] heptalene, four routes to 1, 6, 7, 8, 9, 9a-hexahydro-2H-benzo [c, d] axulen-6-one (19) via the intermediate 4 (l-indanyl) butanoic acid (3) have been investigated:(i) via a Reformatsky reaction of 1-indanone with methyl 4bromo-2-butenoate;(ii) via a Reformatsky reaction of 1-indanone with ethyl bromoacetate and subsequent chain lengthening by a malonic ester alkylation sequence;(iii) via ...