A radical mediated approach to the stereoselective formal total synthesis of (+)-Sch 642305

作者: Tushar Kanti Chakraborty , Rajarshi Samanta , Pulukuri Kiran Kumar , None

DOI: 10.1016/J.TET.2009.06.059

关键词: Chemical synthesisHydroxymethylStereochemistrySynthonStereoselectivityTotal synthesisDouble bondEpoxideChemistryRing (chemistry)Organic chemistryBiochemistryDrug discovery

摘要: A formal total synthesis of (+)-Sch-642305 is described. The synthesis, which commenced from a simple chiral synthon (5S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one, employed, as key step, radical mediated opening epoxy alcohol intermediate with Cp 2 Ti(III)Cl following an efficient method developed by us earlier. resultant was intramolecularly trapped the electron deficient double bond present in molecule to give rise its highly functionalized six-membered carbocyclic ring stereoselective manner.

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