Synthesis of epimeric 2-d1-5.BETA.-pregnane-3,11,20-triones.

• IKEGAWA SHIGEO

• HINO YOSHIHIRO

• SUNAGAWA MASAYUKI

• NAMBARA TOSHIO

Abstract

In order to clarify the stereochemistry of hydrogen loss from the C-2 position during microbial transformation of 5β-pregnane-3, 11, 20-trione into the Δ¹-unsaturated compound, the stereospecific synthesis of epimeric C-2 deuterated substrates has been carried out. A key intermediate, 5β-pregn-2-ene-11α, 20β-diol diacetate, was obtained from the readily available 11α-hydroxyprogesterone through two synthetic routes. The trans-diaxial opening of the 2β, 3β-epoxide with lithium aluminum deuteride provided the 2α-d₁-3β-ol. Deuterioboration of the Δ²-olefin and subsequent oxidation of the organoborane afforded the 2α-d₁-3β-ol. On oxidation with chromium trioxide-pyridine complex, the epimeric 2-d₁-5β-pregnane-3β, 11α, 20β-triols were converted to the desired 2-d₁-5β-pregnane-3, 11, 20-triones.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 27 (8), 1864-1870, 1979

  The Pharmaceutical Society of Japan

Keywords

• epimeric 2-d<SUB>1</SUB>-5β-pregnane-3, 11, 20-triones

Details

• CRID: 1390001204173720448
• NII Article ID: 110003623741
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.27.1864
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/27/8/27_8_1864/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1980085626
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed