Total synthesis of siomycin A: Construction of synthetic segments

Tomonori Mori, Shuhei Higashibayashi, Taiji Goto, Mitsunori Kohno, Yukiko Satouchi, Kazuyuki Shinko, Kengo Suzuki, Shunya Suzuki, Hiraku Tohmiya, Kimiko Hashimoto, Masaya Nakata

研究成果: Article査読

21 被引用数 (Scopus)

抄録

The five practical segments for the total synthesis of siomycin A, that is, the dehydropiperidine segment A (5), the pentapeptide segment B (3), the dihydroquinoline segment C (6), and the β-phenylselenoalanine dipeptide segments D (7) and E (4), were synthesized. Segment A (5) was constructed by the coupling of the azomethine ylide and the chiral sulfinimine, followed by the stereoselective reduction of the six-membered imine function. Segment B (3) was synthesized by the phenylselenylation of the β-lactone, stereoselective vinylzinc addition to the chiral sulfinimine, and oxazoline-thioamide conversion. Segment C (6) was prepared by the one-pot olefination of the tetrahydroquinoline N-oxide using triflic anhydride and triethylamine, stereoselective reduction of the methyl ketone function, and regioselective Yb-OTf)3-catalyzed epoxide opening by the amino group. Segments D (7) and E (4) were synthesized by coupling of the properly protected β-phenylselenoalanines.

本文言語English
ページ(範囲)984-1012
ページ数29
ジャーナルChemistry - An Asian Journal
3
6
DOI
出版ステータスPublished - 2008 6月 2

ASJC Scopus subject areas

  • 生化学
  • 有機化学

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