6-Hydroxycortisol 6-Hemisuccinateの合成

曽根 久雄, 小嶋 正治, 小川 弘

doi:10.1248/yakushi1947.95.2_185

6-Hydroxycortisol 6-Hemisuccinateの合成

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書誌事項

タイトル別名

Syntheses of 6-Hydroxycortisol 6-Hemisuccinate
6 Hydroxycortisol 6 Hemisuccinate ノゴウセ

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抄録

The selective acetylation of 17α, 20, 20, 21-BMD-pregnan-5α, 6β, 11β-triol-3-one (IV), derived from cortisone, was led to its 6β-acetate (V). A solution of V in CHCl₃ containing EtOH (0.7%) was treated with HCI gas to give 17α, 20, 20, 21-BMD-4-pregnene-6α, 11β-diol-3-one-6-acetate (VIa) and in pure CHCl₃ to give 6β-derivative (VIb). The hydrolysis of 6-O-acetate of VIa with K₂CO₃ followed by succinylation with succinic anhydride gave 17α, 20, 20, 21-BMD-4-pregnene-6α, 11β-diol-3-one 6-hemisuccinate (VIIIa). 6α-Hydroxy- cortisol 6-hemisuccinate (IXa) was obtained by the hydrolysis of the bismethylenedioxy protecting group in VIIIa with 50% AcOH. 6β-Hydroxycortisol 6-hemisuccinate (IXb) was also obtained from VIb by the same procedure.