137939-59-4Relevant academic research and scientific papers
Naturally Occurring Spirocyclic Ketals from Lactones. 3
Jacobson, Roy,Taylor, Robert J.,Williams, Howard J.,Smith, Leverett R.
, p. 3140 - 3142 (1982)
Our earlier methodology for the synthesis of 1,6-dioxaspirononane and 1,6-dioxaspirodecane derivatives has been applied to the synthesis of substances found in the mandibular gland secretions of Andrena bees.Use of optically active propylene oxide as a precursor gave 7-methyl-1,6-dioxaspirodecane, reported from Andrena and Vespula species, in 80percent optical purity as shown by 13C NMR spectroscopy with a chiral shift reagent.Adaptations of the method allowed synthesis of a tetramethyl-1,6-dioxaspirononene found in Japanese hop oil and of exogonic acid, a resin constituent of the Brazilian tree Ipomoae operculata (Martin).We have also simplified our synthesis of chalcogran, 2-ethyl-1,6-dioxaspirononane, by using γ-caprolactone and the lithium reagent prepared from 3-bromo-1-propyl 1-ethoxyethyl ether.
