93566-59-7Relevant academic research and scientific papers
Regio- and Stereoselectivity of the Reaction between Cyanocuprates and Cyclopentene Epoxides. Application to the Total Synthesis of Prostaglandins
Marino, Joseph P.,Pradilla, Roberto F. de la,Laborde, Edgardo
, p. 4898 - 4913 (1987)
A systematic study of the reaction between cyclopentene epoxides and alkyl-, alkenyl-, and arylcyanocuprates is described.Alkylcyanocuprates react with complete regio- and stereoselectivity to provide trans-4-alkylcyclopent-2-enols in excellent yields.Vin
Stereocontrolled Synthesis of Prostaglandins from Cyclopentadiene Monoepoxide
Marino, Joseph P.,Pradilla, Roberto Fernandez de la,Laborde, Edgardo
, p. 5279 - 5280 (2007/10/02)
Two complementary syntheses of prostaglandins from the same key intermediate 3, available in four steps from cyclopentadiene monoepoxide, are described.In one approach, a saturated α-chain is introduced via a 1,4-addition of an appropriately functionalized cyanocuprate reagent onto silyl enol ether 3.The resulting prostanoid compound was converted into the bronchodilator 1-decarboxy-1-hydroxymethyl PGE1, PGE1, and PGF1α.The second approach involves the transformation of silyl enol ether 3 into the known prostanoid precursor 11 via selective addition of carbethoxycarbene and subsequent fluoride-induced ring opening of the resulting (silyloxy)cyclopropane carboxylate ester.
