Stereoselective construction of quaternary chiral centers using Ti (III)-mediated opening of 2, 3-epoxy alcohols: studies directed toward the synthesis of penifulvins

TK Chakraborty, AK Chattopadhyay, R Samanta…

Index: Chakraborty, Tushar Kanti; Chattopadhyay, Amit Kumar; Samanta, Rajarshi; Ampapathi, Ravi Sankar Tetrahedron Letters, 2010 , vol. 51, # 33 p. 4425 - 4428

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Citation Number: 8

Abstract

A trisubstituted α, β-unsaturated ester moiety was suitably placed in a molecule also bearing an epoxy alcohol moiety at its other end to intramolecularly trap the intermediate radical, which was formed when the molecule was treated with Cp2Ti (III) Cl to regio-and stereoselectively open its epoxy ring, giving rise to a quaternary chiral center. The method was subsequently used in an attempt to construct the bicyclic core framework of potent ...