An intramolecular furan-diene diels-alder approach to 11-oxo 10α-steroids

Sandra Claeys, Dirk Van Haver, Pierre J. De Clercq, Marco Milanesio, Davide Viterbo

Research output: Contribution to journalArticlepeer-review

Abstract

The intramolecular cycloaddition of 14, with dimethylaluminium chloride as a catalyst and under kinetic control, yielded the exo adduct 19a. Opening of the oxygen bridge in the reduced adduct 20 gave intermediate 21. Oxidation of the latter made it possible to introduce the methyl group at C-10, which exclusively afforded 23, with the unnatural configuration. Further conversion resulted in the formation of D-homo-10-epi-adrenosterone (25).

Original languageEnglish
Pages (from-to)1051-1062
Number of pages12
JournalEuropean Journal of Organic Chemistry
Issue number6
DOIs
Publication statusPublished - 2002
Externally publishedYes

Keywords

  • Cycloadditions
  • Steroid
  • Synthetic methods

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