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

Chakraborty, Tushar Kanti ; Chattopadhyay, Amit Kumar ; Samanta, Rajarshi ; Ampapathi, Ravi Sankar (2010) Stereoselective construction of quaternary chiral centers using Ti(III)-mediated opening of 2,3-epoxy alcohols: studies directed toward the synthesis of penifulvins Tetrahedron Letters, 51 (33). pp. 4425-4428. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2010.06.076

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 insecticides penifulvins.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Penifulvin; Ti(III)-mediated Epoxide Opening; Radical Cyclization; Quaternary Chiral Center
ID Code:69578
Deposited On:14 Nov 2011 03:52
Last Modified:14 Nov 2011 03:52

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