286440-95-7Relevant academic research and scientific papers
METHOD FOR PRODUCING PROSTAGLANDIN DERIVATIVE, PROSTAGLANDIN DERIVATIVE, INTERMEDIATE COMPOUND THEREFOR AND METHOD FOR PRODUCING THE SAME
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Page/Page column 21-22, (2010/02/15)
PROBLEM TO BE SOLVED: To provide a method for producing a prostaglandin derivative, the prostaglandin derivative and an intermediate compound therefor, especially a method for producing a δ-12-prostaglandin J2 derivative using a new method for chemical synthesis through the intermediate compound. SOLUTION: The method for production is a method for producing the prostaglandin derivative using (1R,3R)-4-cyclopentene-1,3-diol 3-acetate (carboxylate) as a starting material. The method is composed of (A) an α-side chain introduction step of providing a malonic acid ester addition compound at the 3-position of the (1R,3R)-4-cyclopentene-1,3-diol, (B) an α-side chain extension step of affording a (1R,3R)-4-cyclopenten-1-one compound having the α-side chain of the prostaglandin derivative at the 3-position and (C) a prostaglandin derivative synthesizing step of conversion into the prostaglandin derivative.
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.
