合成路线:The oxidation of (5R)-(-)-carvone (I) with 3-chloroperbenzoic acid (3-CPB) in dichloromethane gives 5(R)-acetyl-2-methyl-2-cyclohexen-1-one (II),which is condensed with ethyltriphenylphosphonium bromide (III) by means of butyllithium in THF yielding 2-methyl-5(Z)-(1-methyl-1-propenyl)-2-cyclohexen-1-one (IV).The photochemical oxidation of (IV) in acetonitrile catalyzed by methylene blue affords (1R,4RS,5R,8S)-4,8-dimethyl-4-vinyl-2,3-dioxabicyclo[3.3.1]nonan-7-one (V),which is ozonolyzed with O3 in methanol to the corresponding aldehyde as a mixture of enantiomers,which is submitted to crystallization giving the (1S,4R,5R,8S)-isomer (VI).Finally,this compound is submitted to a Wittig condensation with 2,4-bis(trifluoromethyl)benzyltriphenylphosphonium bromide (VII) by means of sodium bis(trimethylsilyl)amide (NaBTSA) in dichloromethane.
参考文献标题:Ro 42-1611 (arteflene),a neweffective antimalarial: Chemical structure and biological activity
文献作者:Hofheinz,W.; B黵gin,H.; Gocke,H.; Jaquet,C.; Masciadri,R.; Schmid,G.; Stohler,H.; Urwyler,H.
参考来源:Trop Med Parasitol 1994,45(3),261-5
合成路线:The oxidation of (5R)-(-)-carvone (I) with 3-chloroperbenzoic acid (3-CPB) in dichloromethane gives 5(R)-acetyl-2-methyl-2-cyclohexen-1-one (II),which is condensed with ethyltriphenylphosphonium bromide (III) by means of butyllithium in THF yielding 2-methyl-5(Z)-(1-methyl-1-propenyl)-2-cyclohexen-1-one (IV).The photochemical oxidation of (IV) in acetonitrile catalyzed by methylene blue affords (1R,4RS,5R,8S)-4,8-dimethyl-4-vinyl-2,3-dioxabicyclo[3.3.1]nonan-7-one (V),which is ozonolyzed with O3 in methanol to the corresponding aldehyde as a mixture of enantiomers,which is submitted to crystallization giving the (1S,4R,5R,8S)-isomer (VI).Finally,this compound is submitted to a Wittig condensation with 2,4-bis(trifluoromethyl)benzyltriphenylphosphonium bromide (VII) by means of sodium bis(trimethylsilyl)amide (NaBTSA) in dichloromethane.
参考文献标题:Arteflene
文献作者:Rabasseda,X.; Mealy,N.; Castar,J.
参考来源:Drugs Fut 1995,20(4),341
产品链接: CAS No. 123407-36-3››