合成路线1

A) Synthesis of intermediate (IX): The reaction of alpha-pinene (I) with paraformaldehyde at 180 C gives 10-hydroxymethyl-2-pinene (II), which by reaction with dihydropyran and p-toluenesulfonic acid in dichloromethane is converted to the tetrahydropyranyl ether (III) The reaction of (III) with diborane in THF affords 10-(tetra-hydropyran-2yloxymethyl)pinan-3-ol (IV), which is oxidized with CrO3 - MnSO4 - H2SO4 in ether to the ketone (V). The stereoselective reduction of (V) with NaBH4 in methanol gives the alcohol (VI), which is mesylated with methanesulfonyl chloride and triethylamine in dichloromethane to the mesyl ester (VII). The reaction of (VII) with sodium azide in HMPT yields the azide (VIII), which by reduction with LiAlH4 in refluxing ethyl ether affords 10-tetrahydropyran-2-yloxymethyl)pinan-3-ylamine (IX).