Tetrahedron p. 6201 - 6206 (1988)
Update date:2022-08-04
Topics:
Mihailovic, Mihailo LJ.
Lorenc, Ljubinka
Dabovic, Milan
Bjelakovic, Mira
The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly in β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ca.7percent yield) and the rearranged 4β-acetoxy-Δ5(10)-unsaturated 9,10-seco-9-ketone (4) as the major product (in 61percent yield).Unexpestedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58percent yield).
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