G. Tolstikov, V. P. Yur'ev, M. Goryaev
Jul 1, 1967
Citations
0
Influential Citations
0
Citations
Journal
Chemistry of Natural Compounds
Abstract
In the present paper we describe A/B-cis-spirosolans obtained from solasodine, which have not been previously studied. When solasodine (I) was oxidized by the Oppenauer method (toluene, cyclohexanone, aluminum isopropoxide), the reaction mixture gave a 70% yield of solasodenone (II), mp 183-184" C; ~2aHxSOH 242 and 304 my (log • 4.24, 2.02). The hydrogenation of II on Pd/CaCO s in ethanol led to two solasodanones, whose configurations were established from their optical rotatory dispersion curves. A/B-cis-solasodanone (III) with mp 164-175" C, k CzHsOH 280 m~t (log 6 max 1.45) has a dispersion curve with a valley at about 310 ml~ which is characteristic for 515-3-ketosteroids [2]; the second ketone has the 5c~-configuration (IV) mp 204-205* C, k~aZaHxsOH 280 m/J (log e 1.38) [aim0 +2800* (peak).