Chemical transformations of the aliphatic portion of the mold metabolite zearalenone were examined. Reactions at the C'-6 ketone and the C'-l double bond and positions adjacent to these reaction centers are reported.The reactions proved to be quite regioselective.
CARBOXYLIC-CARBONIC ANHYDRIDES 1703 is 75°; 20 these authors also reported its conversion to cinnamic acid by boiling hydrochloric acid, a result which we duplicated. A sample of the acid (0.6 g.) was heated to boiling with 25 cc. 6.0N hydrochloric acid and gave, on cooling, crystalline cinnamic acid (0.45 g.), melting point and mixed melting point with authentic cinnamic acid, 130-132°, Oxidation of 2-(8-styryl)-4-methyl-l,3-dioxolane (Via) with peracetic acid catalyzed hy sulfuric acid. To 76 g. (0.4 mole) of 2-(/3-styryl)-4-methyl-l,3-dioxolane containing 0.76 g. of sulfuric acid was added with stirring 157 g. of a 24.3% solution of peracetic acid in ethyl acetate {i.e., containing 38.0 g. or 0.5 mole peracetic acid) over a period of 1 hr. The reaction was exothermic from the outset, and the temperature was maintained at 25-33°b y ice-water cooling. After an additional 4 hr. at 30°, titration for peracetic acid indicated the theoretical amount had been consumed. Sodium acetate, 1.25 g., was added to neutralize the sulfuric acid. Distillation through a glass helix-packed column gave, after recovery of solvent and acetic acid, 23 g. (28% yield) of impure propylene glycol monocinnamate, b.p. ca. 195°/ 1.25 mm., 7iaD°1 .5483.
This review describes approaches for improved preparations of 19‐norsteroids. They are based on novel total syntheses of estrone and on intramolecular functionalization and elimination of the C‐19 methyl group in androstane derivatives.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.