871095-02-2Relevant articles and documents
Access to isocarbacyclin derivatives via substrate-controlled enolate formation: Total synthesis of 15-deoxy-16-(m-tolyl)-17,18,19,20- tetranorisocarbacyclin
Sheddan, Neil A.,Mulzer, Johann
, p. 5115 - 5118 (2007/10/03)
(Chemical Equation Presented) 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 reaction (C5-C6) with a suitable primary alkyl Grignard reagent. Introduction of the C13-C14 (E)-double bond in the ω-side chain is performed by the Julia-Kocienski olefination.