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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