28495-21-8Relevant articles and documents
Synthetic studies towards the Lycopodium alkaloid paniculatine
Lei, Shenghui
, p. 11014 - 11020 (2013/09/02)
Two bridging tetracyclic products have been observed while attempting to construct the final C-ring of the Lycopodium alkaloid, paniculatine, by an intramolecular addition of enolates to unactivated N-alkyl pyridinium salts. The Royal Society of Chemistry 2013.
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.
Synthesis of 4,4-Disubstituted Cyclohexenones. Part 2. Cycloaddition of 2-Chloroacrylonitrile to 5-Substituted 1,3-Dimethoxycyclohexa-1,4-dienes
Clark, Richard S. J.,Holmes, Andrew B.,Matassa, Victor G.
, p. 1389 - 1400 (2007/10/02)
The cycloaddition of 2-chloroacrylonitrile to 1,3-dimethoxycyclohexadienes (3; R1=OMe, R2=H), derived by in situ conjugation of the Birch reduction products (12) produced from aromatic precursors (11) gave after acid work-up mainly bicyclooctanone
