Conclusions
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1.
The reduction of the 17-keto group in ketol (II) with LiAlH4 gives predominantly the 17α-diol (VI), whereas the similar reduction with NaBH4 leads to a mixture of the 17β- and 17α-diols (VII) and (VI) in a 5∶4 ratio.
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2.
The catalytic hydrogenation of diols (VI) and (VII) proceeds stereospecificalty to give the corresponding 3-methyl ethers of the 8α, 9α-estra-3, 14β, 17-triols (VIII) and (X).
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3.
The reduction of the Δ9(11) double bond in diols (VI) and (VII) with sodium in liquid NH3 proceeds in a strictly stereospecific manner to give the corresponding 3-methyl ethers of the 8α, 9β-estra-3, 14β, 17-triols (IX) and (XI).
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4.
The formation of an intramolecular hydrogen bond in the series of 14β, 17β-cis-diols (X) and (XI) depends on the configuration of the hydrogen at C-9.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1158–1163, May, 1975.
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Lailiev, A.O., Koshoev, K.K., Senyavina, L.B. et al. Total synthesis of 14β-hydroxy-8α, 9α- and 14β-hydroxy-8α, 9β-estradiols. Russ Chem Bull 24, 1064–1068 (1975). https://doi.org/10.1007/BF00922966
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DOI: https://doi.org/10.1007/BF00922966