Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues

Akihiro Yoshida, Keiichiro Ono, Yoshitomo Suhara, Nozomi Saito, Hiroaki Takayama, Atsushi Kittaka

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Novel efficient synthesis of several enantio-pure 2-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues through radical introduction of 2-alkyl chain and C5-C6 position coupling using Julia-type olefination as key steps was established starting from commercially available (-)-quinic acid as a chiral pool.

Original languageEnglish
Pages (from-to)1175-1179
Number of pages5
JournalSynlett
Issue number8
Publication statusPublished - 2003
Externally publishedYes

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Quinic Acid
1,25-dihydroxy-19-norvitamin D3

Keywords

  • Coupling
  • Julia reactions
  • Radical reactions
  • Total synthesis
  • Vitamin D

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues. / Yoshida, Akihiro; Ono, Keiichiro; Suhara, Yoshitomo; Saito, Nozomi; Takayama, Hiroaki; Kittaka, Atsushi.

In: Synlett, No. 8, 2003, p. 1175-1179.

Research output: Contribution to journalArticle

Yoshida, Akihiro ; Ono, Keiichiro ; Suhara, Yoshitomo ; Saito, Nozomi ; Takayama, Hiroaki ; Kittaka, Atsushi. / Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues. In: Synlett. 2003 ; No. 8. pp. 1175-1179.
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