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Synthesis of chiloglottones - semiochemicals from sexually deceptive orchids and their pollinators

Poldy, Jacqueline; Peakall, Rodney; Barrow, Russell


A five-step synthesis of monoalkyl- and 2,5-dialkyl-1,3-cyclohexanediones (1) is described via a sequence involving sequential Birch reductions and alkylations from the readily accessible and inexpensive starting material, 3,5-dimethoxybenzoic acid. Two approaches were considered in which alkylation at C-2 occurs either prior or subsequent to the proposed reduction. The successful route, in which Birch reduction of a 3-alkyl resorcinol derivative (3) precedes alkylation was applied in the...[Show more]

CollectionsANU Research Publications
Date published: 2009
Type: Journal article
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/b912233h


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