An 18-acetoxy-substituent inhibits some of the usual reactions of the pregnan-20-one side chain, and causes preferential formation of the Δ17(20)-rather than the usual Δ20(21)-enol acetate with isopropenyl acetate. 20,20′-Anhydro-dimers can arise from an 18-hydroxypregnan-20-one in the 18 → 20-hemiacetal form. The formation and cleavage of 17β,18-cyclo-17α-pregnan-20-ones is described.
D. N. Kirk and M. S. Rajagopalan, J. Chem. Soc., Perkin Trans. 1, 1976, 1064 DOI: 10.1039/P19760001064
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