Issue 12, 2012

Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

Abstract

10-Hydroxy-2E-decenoic (10-HDA) and 9-oxo-2E-decenoic (9-ODA) acids, two components identified in honeybee secretions, have both received considerable recent interest due to their involvement in caste switch and maintenance. Herein we report for the first time a metal-free, gram scale, and stereoselective synthesis of these honeybee secretion components by TEMPO catalyzed oxidation of readily available alcohols and subsequent Doebner–Knoevenagel reactions between the resulting aldehydes and malonic acid. Mechanistic investigations undertaken highlighted the crucial role of the Doebner–Knoevenagel reaction in the high yielding and selective preparation of the α,β-unsaturated acids 10-HDA and 9-ODA. The combination of inexpensive and environmentally friendly reagents with simple synthetic procedures renders this approach a valuable green strategy for the gram scale preparation of these biologically relevant natural molecules.

Graphical abstract: Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

Supplementary files

Article information

Article type
Paper
Submitted
15 Feb 2012
Accepted
12 Mar 2012
First published
13 Mar 2012

RSC Adv., 2012,2, 5229-5233

Straightforward, metal-free, and stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of honeybee (Apis mellifera) secretions

C. Milite, M. Viviano, M. Santoriello, F. Aricò, G. Sbardella and S. Castellano, RSC Adv., 2012, 2, 5229 DOI: 10.1039/C2RA20275A

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