Enantioselective Synthesis of SB-203207

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• 作者：Yasuo Hirooka ; Kazutada Ikeuchi ; Yuichiro Kawamoto ; Yusuke Akao ; Takumi Furuta ; Tomohiro Asakawa ; Makoto Inai ; Toshiyuki Wakimoto ; Tohru Fukuyama ; Toshiyuki Kan
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：March 21, 2014
• 年：2014
• 卷：16
• 期：6
• 页码：1646-1649
• 全文大小：295K
• 年卷期：v.16,no.6(March 21, 2014)
• ISSN：1523-7052

文摘

Total synthesis of SB-203207 (1) was achieved, beginning with a desymmetrical C鈥揌 insertion reaction of a diazoester bearing our recently developed chiral auxiliary. Utilizing the optically active bicyclo[3.3.0]octane ring, four stereogenic centers were efficiently constructed in sequence. Finally, mild oxidation of 27 to carboxylic acid via a cyanohydrin intermediate and hydrolysis of cyanide to carboxyamide in the presence of the labile enamide group completed an efficient total synthesis of 1.