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

Research output: Contribution to journalArticle

20 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

Fingerprint

Thioamides
Imines
Dipeptides
Epoxy Compounds
Lactones
Ketones
Oxides
sulfinimine
siomycin A
triethylamine
azomethine
triflic anhydride
ytterbium(III) triflate
1,2,3,4-tetrahydroquinoline

Keywords

  • Heterocycles
  • Peptides
  • Siomycin A
  • Stereoselectivity
  • Sulfinimines

ASJC Scopus subject areas

  • Chemistry(all)
  • Medicine(all)

Cite this

Total synthesis of siomycin A : Construction of synthetic segments. / Mori, Tomonori; Higashibayashi, Shuhei; Goto, Taiji; Kohno, Mitsunori; Satouchi, Yukiko; Shinko, Kazuyuki; Suzuki, Kengo; Suzuki, Shunya; Tohmiya, Hiraku; Hashimoto, Kimiko; Nakata, Masaya.

In: Chemistry - An Asian Journal, Vol. 3, No. 6, 02.06.2008, p. 984-1012.

Research output: Contribution to journalArticle

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, vol. 3, no. 6, pp. 984-1012. https://doi.org/10.1002/asia.200800032
Mori, Tomonori ; Higashibayashi, Shuhei ; Goto, Taiji ; Kohno, Mitsunori ; Satouchi, Yukiko ; Shinko, Kazuyuki ; Suzuki, Kengo ; Suzuki, Shunya ; Tohmiya, Hiraku ; Hashimoto, Kimiko ; Nakata, Masaya. / Total synthesis of siomycin A : Construction of synthetic segments. In: Chemistry - An Asian Journal. 2008 ; Vol. 3, No. 6. pp. 984-1012.
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