Synthetic studies on thiostrepton family of peptide antibiotics: synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins |
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| Authors: | Tomonori Mori Kimiko Hashimoto Masaya Nakata |
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| Institution: | Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan |
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| Abstract: | Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins, members of the thiostrepton family of peptide antibiotics, has been achieved featuring the one-pot olefination via the Matsumura-Boekelheide rearrangement “using trifluoromethanesulfonic anhydride and triethylamine” and the stereoselective addition reaction controlled by the stereocenter of the peri-position. |
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| Keywords: | Thiostrepton Siomycins Dihydroquinoline Matsumura-Boekelheide rearrangement Stereoselective addition |
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