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Total Synthesis of Siomycin A: Completion of the Total Synthesis

Total Synthesis of Siomycin A: Completion of the Total Synthesis

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

Chem Asian J. 2008 Jun 2;3(6):1013-25.

PMID: 18464235

Abstract:

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 beta-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 beta-phenylselenoalanine dipeptide segment E (6) at the segment A portion), thus furnishing siomycin A (1).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP12656096	Siomycin A		12656-09-6	Price

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