Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3

Kosuke Usuda, Tanima Biswas, Takuya Yamaguchi, Yusuke Akagi, Koji Yasui, Motonari Uesugi, Isao Shimizu, Seijiro Hosokawa, Kazuo Nagasawa

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

1β,3β,25-Dihydroxy-19-norvitamin D3 (4a) and 1α,3α,25-dihydroxy-19-norvitamin D3 (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(-)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia-Kocienski olefination to construct the diene unit. The structures of the products were confirmed by 1H-NMR and nuclear Overhauser effect (NOE) experiments.

Original languageEnglish
Pages (from-to)1190-1195
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume64
Issue number8
DOIs
Publication statusPublished - 2016

Keywords

  • 19-Norvitamin D
  • Julia-Kocienski coupling
  • cis-A ring synthon

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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