75222-60-5Relevant academic research and scientific papers
Terpenoid Chemistry. XXIV (1R)-1-Methoxymyodesert-3-ene, an Iridoid Constituent of Myoporum deserti (Myoporaceae)
Grant, Hamish G.,O'Regan, Peter J.,Park, Robert J.,Sutherland, Maurice D.
, p. 853 - 878 (2007/10/02)
A common variety of Myoporum deserti A.Cunn. (Ellangowan Poison Bush) yields an essential oil consisting largely of the iridoid monoterpene, (1R)-1-methoxymyodesert-3-ene, C11H18O2, (1R,4aS,7R,7aR)-1-methoxy-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopentapyran, b.p. 67 deg/2 mm, D - 165 deg.This cyclic acetal is hydrolysed to methanol and a mixture of two epimeric cyclopentanoid dialdehydes which are oxidized to the two epimeric trans, trans-nepetalinic acids and yield (+)-(R)-actinidine with Brady's reagent, (1R)-1-Methoxymyodesert-3-ene is oxidized by ozone/hydrogen peroxide to (1R,2R,5R)-2-acetyl-5-methylcyclopentanecarboxylic acid.Hydrogenation yields mainly (1R)-methoxymyodesertan, hydrolysed by aqueous maleic acid at room temperature to methanol and a cyclic hemiacetal, (1R,4R,4aR,7R,7aR)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol.Oxidation of this cis,cis-hemiacetal by bromine in acetate buffer yields a lactone further oxidized by chromic acid to (2R,1',S',2'R,3'R)-2-(2'-carboxy-3'-methylcyclopentyl)-propionic acid. (1R)-1-Methoxymyodesertan, refluxed with aqueous phthalic acid, yields (+)-(4R,4aR,7R)-4,7-dimethyl-3,4,4a,5,6,7-hexahydrocyclopentapyran.Treatment of the hexahydropentapyran, the cis,cis-hemiacetal or (1R)-1-methoxymyodesertan with hydrochloric acid yields a trans,trans-hemiacetal, (1R,4R,4aR,7R,7aS)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol,which equilibrates in solution to a mixture of α- and β-anomers.Spectral studies of these and other products establish the configuration of the natural product at C1. (1R)-1-Methoxymyodesert-3-ene is not toxic to sheep as are the β-substituted furans characteristic of most other chemovarieties of M. deserti.
