Issue 29, 2012

Synthesis of CDE molecular fragments related to sendanin mediated by titanocene(iii)

Abstract

A practical, brief, and diastereoselective synthesis of limonoid CDE fragments from a readily available starting material is described. The key step was the titanocene(III)-promoted cyclization of unsaturated epoxylactones, readily prepared from α-cyclocitral. In this way, we confirm the viability of our procedure for the synthesis of a limonoid model with different functionalization patterns. We also report the antifeedant activity of epoxylactones 18 and 19, which show significant antifeedant activity against Spodoptera littoralis and Spodoptera frugiperda, two insect species with different feeding ecologies.

Graphical abstract: Synthesis of CDE molecular fragments related to sendanin mediated by titanocene(iii)

Supplementary files

Article information

Article type
Paper
Submitted
12 Mar 2012
Accepted
30 May 2012
First published
01 Jun 2012

Org. Biomol. Chem., 2012,10, 5620-5628

Synthesis of CDE molecular fragments related to sendanin mediated by titanocene(III)

A. Fernández-Mateos, A. I. Ramos Silvo, R. Rubio González and M. S. J. Simmonds, Org. Biomol. Chem., 2012, 10, 5620 DOI: 10.1039/C2OB25538C

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