53771-32-7Relevant academic research and scientific papers
Efficient synthesis of octandrenolone and related dipyranoacetophenones
Pernin,Muyard,Bevalot,Tillequin,Vaquette
, p. 245 - 247 (2000)
Octandrenolone (1) was prepared in high yield by condensation of 2',4',6'-trihydroxyacetophenone with 3-chloro-3-methylbut-1-yne in the presence of a catalytic amount of copper(I) iodide. Methylation of 1 afforded O-methyloctandrenolone (2). Oxidation of 2 with m-chloroperoxybenzoic acid followed by hydrolysis gave the racemic trans-(+)-1-(9,10-dihydro-9,10- dihydroxy-5-methoxy-2,2,8,8-tetramethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-6- yl)ethanone (3), which confirmed the structure of the natural product previously isolated from Melicope erromangensis.
