57641-76-6Relevant academic research and scientific papers
Synthesis of chiloglottones - Semiochemicals from sexually deceptive orchids and their pollinators
Poldy, Jacqueline,Peakall, Rod,Barrow, Russell Allan
supporting information; experimental part, p. 4296 - 4300 (2009/12/06)
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 synthesis of chiloglottone 1 (1dc), in 58% overall yield. Chiloglottone 1 is a member of a new class of natural products, representing a known sex pheromone of the thynnine wasp Neozeleboria cryptoides and pollinator attractant in the Australian sexually deceptive orchid genus Chiloglottis. The synthetic homologues were assessed for their biological activity via electroantennographic detection.
Total synthesis of angucyclines. Part 15: A short synthesis of (±)-6- deoxybrasiliquinone B
Krohn, Karsten,Micheel, J?rg,Zukowski, Mariola
, p. 4753 - 4758 (2007/10/03)
The 6-deoxybrasiliquinones 2 and 14a were prepared by a boron triacetate mediated Diels-Alder reaction of juglone (9) with the crude mixture of ethoxy dienes 6 and 7. The primary non-aromatic Diels-Alder product 10 was isolated after reaction of the dienol 8 with 9. Dimethyldioxirane oxidation of 10 afforded the epoxide 11. (C) 2000 Elsevier Science Ltd.
