TY  - BOOK
AU  - Bianchi,Ennio
AU  - Djerassi,Carl
AU  - Budzikiewicz,Herbert
AU  - Sato,Yoshio
TI  - Structure of Tomatillidine
KW  - TOMATILLIDINE
N2  - 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
UR  - https://drive.google.com/file/d/1eoe1p-RTYvQ7AlQPzMZX6z3TZkfIfGG_/view?usp=drivesdk
ER  -