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Citation: ZHANG He-Sheng, William Kitching. Synthesis of 2,8-Dimethyl-1,7-dioxaspiroundecane[J]. Chinese Journal of Applied Chemistry, ;2002, 19(4): 404-406. shu

Synthesis of 2,8-Dimethyl-1,7-dioxaspiroundecane

ZHANG He-Sheng ^a,b,, ,
William Kitching ^b

1.
a Faculty of Chemistry and Material Science, Hubei University, Wuhan 430062;
2.
b Department of Chemistry, The University of Queensland, Brisbane, Qld 4072, Australia

Corresponding author: ZHANG He-Sheng,
Received Date: 30 June 2001
Available Online: 4 December 2001

Alkylation of diethyl 3-oxoglutarate monoanion by 4-bromobutene to produce enone diester 3, subsequent alkylation of 3 with 4-bromo-1-butene using K₂CO₃ and a catalytic amount of NaIin the mixed solvent afforded dienone diester 4, which underwent decarboxylative hydrolysis when treated with 15% KOH in methanol under refluxing to provide dienone 5. The dienone afforded 2,8-dimethyl-1,7-dioxaspiroundecane 1 in good yield and high purity via an oxymercuration-cyclisation-reduction sequence.
- spiroketal,
- fruit fly pheromone,
- synthesis
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