Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids

Miyu Furuta, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Steroid family has various bioactivities and characteristic polycyclic structure. Although several synthetic methods have been reported, more efficient way is desired for medicinal chemistry. In this Letter, we synthesized pseudoenantiomers of tricyclic enones toward both enantiomers for ABC-ring moiety of steroids utilizing d-mannitol as a chiral source. The key steps are radical domino cyclization of polyalkenyl-β-keto ester into tricyclic keto ester and subsequent dealkoxycarbonylation.

Original languageEnglish
Pages (from-to)3189-3191
Number of pages3
JournalTetrahedron Letters
Volume55
Issue number20
DOIs
Publication statusPublished - 2014 May 14
Externally publishedYes

Keywords

  • Dealkoxycarbonylation
  • Domino reaction
  • Radical cyclization
  • Steroid
  • β-Keto ester

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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