Abstract
Strophanthidin differs from other cardiac genins in that an aldehyde group is present on C atom 10. Strophanthidol was prepared by treating a hot soln. of 5 g. of anhydrous strophanthidine in a mixture of 50 cc. of isopropyl alcohol and 150 cc. of benzol with 88 cc. of an isopropyl alcoholic soln. of Al-isopropylate (8.8 g.). The mixture was heated about 6 hrs., during which time about 350 cc. of the soln. was distilled. The vol. of the boiling soln. was kept constant by continuous addition of the isopropyl alcohol benzol mixture. 90 cc. MeOH and 10 cc. H2O were added to the reaction mixture which was then filtered. The filtrate was evaporated to dryness, the residue extracted with CHCl3 from which 0.9 g. strophanthidol (C23H34O6) crystallized. Strophanthidol was also prepared by the action of 10 g. of amalgamated Al in 380 cc. of 96% alc. on 10 g. of strophanthidin at room temp. The product crystallized from CHCl3 in clusters of needles, m. 222-3[degree], (a)D22= +37.1[degree]. Strophanthidol diacetate formed large prisms, m. 193-5[degree]. By the action of PtO2 on strophanthidol, dihydrostrophanthidol was obtained, m. 207-8[degree], (a)D25= +35.5[degree]. K-strophanthol-7 and its heptaacetate were also prepared. Acid hydrolysis of k-strophanthol-7 gave strophanthotriose. Acetylation of k-strophanthol-7 in pyridine gave an octaacetate, m. 153-5[degree]. If the latter compound was saponified with Ba-methylate, 7 acetyl groups were split off and 18-acetyl-k-strophanthol-7, m. 190-5[degree], obtained.