Hydroboration of 17β-hydroxy-3-methyleneandrost-4-ene gives 3β-hydroxymethyl-5α-androstan-4α,17β-diol whilst, contrary to previous reports, hydroboration of a steroidal 3,5-diene and a 4,6-diene affords not only the 4α,6α-diol but also the 3β,6β- and 4β,6α-diols from the 3,5-diene and the 4β,6α- and 4β,7β-diols from the 4,6-diene.
J. A. Boynton, J. R. Hanson and M. D. Liman, J. Chem. Res. (S), 1998, 376 DOI: 10.1039/A801591K
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