Ynenol lactones: synthesis and investigation of reactions relevant to their inactivation of serine proteases

…, E Thomas, VJ Robinson, A Krantz

Index: Spencer, Robin W.; Tam, Tim Fat; Thomas, Everton; Robinson, Valerie J.; Krantz, Allen Journal of the American Chemical Society, 1986 , vol. 108, # 18 p. 5589 - 5597

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Citation Number: 72

Abstract

R'-2-propynylidene)-3-R-tetrahydro-2-pyrones; R= H, alkyl, benzyl; R'= H, alkyl, phenyl] which are designed as serine protease suicide substrates have been accomplished. E ynenol lactones are prepared via iodolactonization of w-hexynoic and w-pentynoic acids, followed by the C~ I/Et~ N/PdCl~(PPh~)~-mediated coupling of the resulting E iodo enol lactones with appropriate alkynes. Isomerization of E iodo enol lactones gives the Z ...