Total synthesis of borrelidin |
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| Authors: | Nagamitsu Tohru Takano Daisuke Marumoto Kaori Fukuda Takeo Furuya Kentaro Otoguro Kazuhiko Takeda Kazuyoshi Kuwajima Isao Harigaya Yoshihiro Omura Satoshi |
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| Institution: | School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan. |
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| Abstract: | The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2.Et2O-mediated chelation-controlled allylation. |
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