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

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21 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)984-1012
Number of pages29
JournalChemistry - An Asian Journal
Volume3
Issue number6
DOIs
Publication statusPublished - 2008 Jun 2

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Keywords

  • Heterocycles
  • Peptides
  • Siomycin A
  • Stereoselectivity
  • Sulfinimines

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

Mori, T., Higashibayashi, S., Goto, T., Kohno, M., Satouchi, Y., Shinko, K., Suzuki, K., Suzuki, S., Tohmiya, H., Hashimoto, K., & Nakata, M. (2008). Total synthesis of siomycin A: Construction of synthetic segments. Chemistry - An Asian Journal, 3(6), 984-1012. https://doi.org/10.1002/asia.200800032