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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Efficient synthesis of octandrenolone and related dipyranoacetophenones.

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.[1]

References

  1. Efficient synthesis of octandrenolone and related dipyranoacetophenones. Pernin, R., Muyard, F., Bévalot, F., Tillequin, F., Vaquette, J. J. Nat. Prod. (2000) [Pubmed]
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