Abstract
Following derivatives were prepared from Substance F, m.p. 183-185°, C21H25O5N, isolated from white meadow saffron corm. Monoacetate (II), m.p. 227-229°, [α]D17: -232°, C23H27O6N; monomethyl compound (III), m.p. 200-203°, [α]D20: -106°, C22H27O5N; nitroso compound (IV), m.p. 187-190°, [α]D20: -99°, C21H24O6N2. Hydrolysis of Substance F with diluted hydrochloric acid gave the demethylated compound (V), m.p. 132-135°, [α]D17: -226°, C20H23O5N. Similar hydrolysis of (II) gave C22H25O5N (VI), m.p. 189-190°, [α]D20: -279°, and of (III), C21H25O5 (VII), m.p. 129-131°, [α]D22: -225°. Treatment of Substance F with conc. ammonia yielded an amino compound (VIII), m.p. 128-131° (decomp.), [α]D22: -133°, C20H24O4N2⋅1/2 CH3OH. Amination of (II) in a similar manner gave C22H26O5N2⋅1/2CH3COCH3 (IX), m.p. 122-125° (decomp.), [α]D22: -293°.
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