The oxidation of khelline (I) with nitric acid gives khellinequinone (II), which is reduced with SO2 yielding khellinequinol (III). The condensation of (III) with epichlorohydrin (IV) affords the 2,3-epoxypropyl ether of khellinequinol (V) (1), which is condensed with benzylisopropylamine (VI) by heating at 110 C giving 3-benzylisopropylamino-2-hydroxypropyl ether of khellinequinol (VII). Finally this compound is debenzylated by reduction with H2 over Pd/C in methanol - acetic acid (1,2). Compound (V) can also be obtained by direct reaction of khellinequinol (III) with 3-(benzylisopropvlamino)-2-hydroxy-1-chloropropane (VIII) by means of NaH in refluxing ethanol (1,2).

The oxidation of khelline (I) with nitric acid gives khellinequinone (II), which is reduced with SO2 yielding khellinequinol (III). The condensation of (III) with epichlorohydrin (IV) affords the 2,3-epoxypropyl ether of khellinequinol (V) (1), which is condensed with benzylisopropylamine (VI) by heating at 110 C giving 3-benzylisopropylamino-2-hydroxypropyl ether of khellinequinol (VII). Finally this compound is debenzylated by reduction with H2 over Pd/C in methanol - acetic acid (1,2). Compound (V) can also be obtained by direct reaction of khellinequinol (III) with 3-(benzylisopropvlamino)-2-hydroxy-1-chloropropane (VIII) by means of NaH in refluxing ethanol (1,2).

The oxidation of khelline (I) with nitric acid gives khellinequinone (II), which is reduced with SO2 yielding khellinequinol (III). The condensation of (III) with epichlorohydrin (IV) affords the 2,3-epoxypropyl ether of khellinequinol (V) (1), which is condensed with benzylisopropylamine (VI) by heating at 110 C giving 3-benzylisopropylamino-2-hydroxypropyl ether of khellinequinol (VII). Finally this compound is debenzylated by reduction with H2 over Pd/C in methanol - acetic acid (1,2). Compound (V) can also be obtained by direct reaction of khellinequinol (III) with 3-(benzylisopropvlamino)-2-hydroxy-1-chloropropane (VIII) by means of NaH in refluxing ethanol (1,2).