Synthetic and Mechanistic Studies on the Azabicyclo [7.3. 1] enediyne Core and Naphtho [2, 3-h] quinoline Portions of Dynemicin A

P Magnus, SA Eisenbeis, RA Fairhurst…

Index: Magnus, Philip; Eisenbeis, Shane A.; Fairhurst, Robin A.; Iliadis, Theodore; Magnus, Nicholas A.; Parry, David Journal of the American Chemical Society, 1997 , vol. 119, # 24 p. 5591 - 5605

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Citation Number: 44

Abstract

The synthesis of the 13-keto-10-azabicyclo [7.3. 1] enediyne core structure of dynemicin A has been achieved by two routes, Schemes 4 and 6. The chemistry of the 13-keto core structure is dominated by the unusually facile bridgehead enolization. Comparison of the rates of cycloaromatization of a variety of enediynes revealed that substantial rate differences occurred even though the distance between the bonding acetylenes was ...