Total synthesis of siomycin A: Completion of the total synthesis

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

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


The total synthesis of siomycin A (1), a representative compound of the thiostrepton family of peptide antibiotics, was achieved by incorporating the five synthetic segments A (2), B (3), C (4), D (5), and E (6). The dehydropiperidine segment A (2) was esterified with the dihydroquinoline segment C (4), and the subsequent coupling with the β-phenylselenoalanine dipeptide segment D (5) at the segment C portion followed by lactamization between the segments A and D gave segment A-C-D (27). This was amidated with the pentapeptide segment B( 3) at the segment A portion followed by one-pot cyclization (between segments A and B) and elongation (with the β-phenylselenoalanine dipeptide segment E (6) at the segment A portion), thus furnishing siomycin A (1).

Original languageEnglish
Pages (from-to)1013-1025
Number of pages13
JournalChemistry - An Asian Journal
Issue number6
Publication statusPublished - 2008 Jun 2


  • Cyclization
  • Epoxides
  • Natural products
  • Siomycin A
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry


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