96849-99-9Relevant articles and documents
Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and γ-cyclogeraniol
Serra, Stefano,Gatti, Francesco G.,Fuganti, Claudio
experimental part, p. 1319 - 1329 (2009/12/01)
A comprehensive study on the lipase PS-mediated resolution of different hydroxy-geraniol isomers is reported. A number of α-, β- and γ-isomers bearing a 2-, 3- or 4-hydroxy functional group were synthesised regioselectively and then submitted to the lipase-mediated kinetic acetylation. The latter experiments showed that the 2-hydroxy isomers 4, 5 and 14 (α, γ and β, respectively) as well as cis-3-hydroxy α-cyclogeraniol 7 and cis-4-hydroxy γ-cyclogeraniol 10 could be easily resolved by this procedure. The enantiomeric purity of the main part of these compounds was increased by recrystallisation and the enantiopure diols obtained were used as building blocks for the synthesis of the natural terpenoids karahana lactone, karahana ether and crocusatin C and for the preparation of the synthetic intermediate γ-cyclogeraniol. The absolute configurations of the enantiomers of the diols 7, 10, 14 and 19 were determined by chemical correlation with the known compounds 40, 41, 39 and 41, respectively.
A New Synthetic Route to (+/-)-Strigol
Dailey, Oliver D.
, p. 1984 - 1989 (2007/10/02)
A new more facile synthetic route to strigol, a potent weed seed germination stimulant, utilizes as starting material ethyl 4-oxo-2,6,6-trimethylcyclohex-2-ene-1-carboxylate (2), obtained by the condensation of mesityl oxide and ethyl acetoacetate.Compound 2 was converted in six steps in 38percent overall yield to the previously reported strigol intermediate, 1,4-dioxo-7,7-dimethyl-4,5,6,7-tetrahydro-2-indanacetic acid (11).The new approach is based upon inexpensive starting materials and reagents and is suitable for large-scale production.The key features of the synthesis include reduction of enone 2 to olefin 5 with triethylsilane and boron trifluoride etherate and a one-pot conversion of ethyl 2-(bromomethyl)-6,6-dimethyl-3-oxocyclohex-1-ene-1-carboxylate (10) to the diketo acid 11.