Structure of Tomatillidine

Tipo de material: Texto

TextoSeries ; Journal of Organic Chemistry, 30(3), p.754-760, 1965Trabajos contenidos:

Bianchi, Ennio
Djerassi, Carl
Budzikiewicz, Herbert
Sato, Yoshio

Tema(s):

TOMATILLIDINE

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Resumen: Tomatillidine (I)subjected to Wolff-Kishner reduction gave deoxotomatillidine (VII), which afforded dihydrodeoxotomatillidine (VIII)by catalytic hydrogenation. VIII was converted into 0,N-diacetyl-A22 dihydrodeoxotomatillidine, (X)by treatment with acetic anhydride, then into 3/3-acetoxy-26-acetylaminocholestan-22-one (XII), by acid hydrolysis. The latter (XII)yielded 3/3-acetoxybisnorallocholanic acid (XIV)by chromic acid oxidation. Selenium dehydrogenation of deoxotomatillidine (VII)afforded a 2,5-disubstituted pyridine derivative which aided in the elucidation of the structure of the basic moiety of the molecule. Mass spectral patterns of hexahydrotomatillidine (III), tetrahydrodeoxotomatillidine (XV), deoxotomatillidine (VII), tomatillidine (I), its O-acetyl derivative (la), and dihydrotomatillidine (II)and spectral data (ultraviolet, infrared, and n.m.r.)of O,N diacetyltomatillidine (VI)showed the location of the carbonyl group.

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Tomatillidine (I)subjected to Wolff-Kishner reduction gave deoxotomatillidine (VII), which afforded dihydrodeoxotomatillidine (VIII)by catalytic hydrogenation. VIII was converted into 0,N-diacetyl-A22 dihydrodeoxotomatillidine, (X)by treatment with acetic anhydride, then into 3/3-acetoxy-26-acetylaminocholestan-22-one (XII), by acid hydrolysis. The latter (XII)yielded 3/3-acetoxybisnorallocholanic acid (XIV)by chromic acid oxidation. Selenium dehydrogenation of deoxotomatillidine (VII)afforded a 2,5-disubstituted pyridine derivative which aided in the elucidation of the structure of the basic moiety of the molecule. Mass spectral patterns of hexahydrotomatillidine (III), tetrahydrodeoxotomatillidine (XV), deoxotomatillidine (VII), tomatillidine (I), its O-acetyl derivative (la), and dihydrotomatillidine (II)and spectral data (ultraviolet, infrared, and n.m.r.)of O,N diacetyltomatillidine (VI)showed the location of the carbonyl group.

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