Access to Isocarbacyclin Derivatives via Substrate-Controlled Enolate Formation: Total Synthesis of 15-Deoxy-16-(m-tolyl)-17, 18, 19, 20-tetranorisocarbacyclin

NA Sheddan, J Mulzer

Index: Sheddan, Neil A.; Mulzer, Johann Organic Letters, 2005 , vol. 7, # 23 p. 5115 - 5118

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Citation Number: 14

Abstract

We describe a convergent and flexible synthesis of 15-deoxy-16-(m-tolyl)-17, 18, 19, 20- tetranorisocarbacyclin (15-deoxy-TIC), a simple isocarbacyclin derivative. The synthesis takes advantage of two key step reactions: a regioselective deprotonation of the described ketone under substrate control which is then trapped, as the enol triflate, to generate the C6- C9α endocyclic double bond, followed by an sp2-sp3 Pd-catalyzed cross-coupling ...