Total synthesis of mycestericin A |
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| Authors: | Hideyuki Sato Masatoshi Iida Takeshi Oishi |
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| Institution: | a Department of Applied Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
b School of Medicine, Keio University, 4-1-1 Hiyoshi, Kohoku-ku, Yokohama 223-8521, Japan |
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| Abstract: | The first total synthesis of mycestericin A (1) starting from tartrates is described. The Overman rearrangement of an allylic trichloroacetimidate generated a tetra-substituted carbon with nitrogen, and subsequent stereoselective transformations afforded the highly functionalized vinyl iodide. The cross-coupling of the vinyl iodide with a chiral organozinc species under Negishi conditions, followed by deprotection, completed the total synthesis of 1. |
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| Keywords: | Mycestericin A Immunosuppressant Total synthesis Overman rearrangement Negishi coupling |
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