Synthesis of a chiral steroid ring D precursor starting from carvone

S. Pogrebnoi, F.C.E. Sarabèr, B.J.M. Jansen, Æ. de Groot

Research output: Contribution to journalArticleAcademicpeer-review

19 Citations (Scopus)

Abstract

A chiral five-membered, silyl enol ether containing, steroid ring D precursor has been synthesized front carvone. This silyl enol ether has been applied in the synthesis of a chiral C17 functionalized steroid skeleton using the addition of a carbocation, generated with ZnBr2 from a Torgov reagent, followed by cyclization of the adduct by treatment with acid.
Original languageEnglish
Pages (from-to)1743-1748
JournalTetrahedron
Volume62
Issue number8
DOIs
Publication statusPublished - 2006

Keywords

  • enantioselective synthesis
  • reductive cleavage
  • building-block
  • cd ring
  • vitamin-d3
  • (r)-2,3-o-isopropylideneglyceraldehyde
  • rearrangement
  • route
  • (s)-2,3-o-isopropylideneglyceraldehyde
  • induction

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