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Transformed steroids

195. Introduction of the 9α-hydroxygroup into Δ5-3β-hydroxysteroids byCircinella sp. mold


A preparative method for 9a-hydroxylation of Δ5-3β-hydroxysteroids using the fungi ofCircinella sp. 10Kh-1220 not capable of modifying theA ring has been developed. It is established that the yields of the main and the side products greatly depend on the transformation conditions, mycelium age, and the structure of the steroid substrate. Under the optimal transformation conditions novel 9α-hydroxysubstituted derivatives of androstenolone, pregnenolone, 16-dehydro-16α,17α-epoxy-, and-16α-methoxypregnenolone have been obtained in 36–80 % yields.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 737–743, April, 1994.

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Voishvillo, N.E., Istomina, Z.I. & Kamernitsky, A.V. Transformed steroids. Russ Chem Bull 43, 689–695 (1994).

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Key words

  • hydroxylation
  • Δ5-3β-hydroxysteroids
  • Δ5-3β,9α-dihydroxysteroids
  • Circinella sp.