Total Synthesis of Borrelidin

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• 作者：Tohru Nagamitsu ; Daisuke Takano ; Kaori Marumoto ; Takeo Fukuda ; Kentaro Furuya ; Kazuhiko Otoguro ; Kazuyoshi Takeda ; Isao Kuwajima ; Yoshihiro Harigaya ; and ; Satoshi //pubs.acs.org/images/en
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：April 13, 2007
• 年：2007
• 卷：72
• 期：8
• 页码：2744 - 2756
• 全文大小：471K
• 年卷期：v.72,no.8(April 13, 2007)
• ISSN：1520-6904

文摘

The total synthesis of borrelidin has been achieved. The best feature of our synthetic route ismacrocyclization at C11-C12 for the construction of an 18-membered ring after esterification betweentwo segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediatedintramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segmentswere synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr₂·Et₂O-mediated chelation-controlled allylation.