Total Synthesis of Siomycin A: Completion of the Total Synthesis |
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| Authors: | Tomonori Mori Dr Shuhei Higashibayashi Dr Taiji Goto Mitsunori Kohno Yukiko Satouchi Kazuyuki Shinko Kengo Suzuki Shunya Suzuki Hiraku Tohmiya Kimiko Hashimoto Prof Dr Masaya Nakata Prof Dr |
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| Institution: | 1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3‐14‐1 Hiyoshi, Kohoku‐ku, Yokohama 223‐8522, Japan, Fax: (+81)?45‐566‐1551;2. Current address: Research Center for Molecular‐Scale Nanoscience, Institute for Molecular Science, Okazaki 444‐8787, Japan;3. Current address: Kyoto Pharmaceutical University, 1 Shichono‐cho, Misasagi, Yamashina‐ku, Kyoto 607‐8412, Japan, Fax: (+81)?75‐595‐4763 |
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| 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 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 ). |
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| Keywords: | cyclization natural products epoxides siomycin A total synthesis |
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