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Effects of Propargylic Substitution and Annelation on the Cycloaromatization of a Bicyclo[7.3.1] Enediyne

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journal contribution
posted on 14.05.1999, 00:00 by David K. Moss, John D. Spence, Michael H. Nantz
The cycloaromatization kinetics of two bicyclo[7.3.1] enediynes are presented. Silyl protection of a propargylic alcohol positioned on the enediyne core was found to moderate enediyne cycloaromatization. However, the presence of multiple fused ring systems exerts geometrical constraints that prevent cycloaromatization of the otherwise facile cyclization previously observed for the core system.