Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones
Date
2008
Authors
Poldy, Jacqueline
Peakall, Rodney
Barrow, Russell
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Volume Title
Publisher
Elsevier
Abstract
Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.
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Keywords
Keywords: 2 ethyl 5 propyl 1,3 cyclohexanedione; acid anhydride; cyclohexane derivative; pheromone; unclassified drug; article; carbon nuclear magnetic resonance; controlled study; nonhuman; Orchidaceae; pollination; pollinator; polymerization; synthesis; wasp; Chi Chiloglottis; Cyclohexanedione; Neozeleboria; Organocadmium reagents; Pheromone; Sexual deception
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Source
Tetrahedron Letters
Type
Journal article
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Restricted until
2037-12-31
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