Arteflene

Arteflene

CAS : 123407-36-3 (Z-form)

 [1S-[1a,4b(Z),5a,8b]]-4-[2-[2,4-Bis(trifluoromethyl)phenyl]ethenyl]-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]nonan-7-one

(1S,4R,5R,8S)-4-[(Z)-2,4-bis(trifluoromethyl)styryl]-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]nonan-7-one

Manufacturers’ Codes: Ro-42-1611

Properties: Crystalline stable material, mp 124°. Highly lipophilic, not sol in water. Stable in soln except in the presence of strong bases or strong reducing agents.

Melting point: mp 124°

Therap-Cat: Antimalarial

 

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.

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