Bufadienolides. IV. A New Route to Pregnane Series from Resibufogenin

概要

論文の詳細を見る
In the previous paper, it was reported that the treatment of resibufogenin (I) with sodium borohydride gave 14β, 15β-epoxy-5β-chol-20 (22)-en-3β, 21,24-triol (III) in a good yield. Therefore, it is considered that the cleavage reaction of a side chain double bond of III might be led to pregnane derivatives. After III was acetylated, the triacetate (IV) obtained was ozonized at -60° to give 14β, 15β-epoxy-20-oxo-5β-pregnane-3β, 21-diyl diacetate (V). This was confirmed by the elemental analyses and spectral data. Then, partial hydrolysis of V with potassium bicarbonate yielded 3-monoacetate (VI). The treatment of VI with periodic acid, followed by usual methylation gave the known methyl 3β-acetoxy-14β, 15β-epoxy-5β-androstane-17-carboxylate (VII). The identity was established by comparison with the authentic sample, which was prepared independently from acetyl-resibufogenin (II) by the method of Linde and Meyer. The success of the three-step conversion of resibufogenin to a pregnane derivatives (V), which proceeded in a 50% overall yield, opened a new route to pregnane derivatives having A/B- and C/D-cis ring system.
公益社団法人日本薬学会の論文
1969-06-25