Total Synthesis of Kendomycin Featuring Intramolecular Dtz Benzannulation

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• 作者：Kyosuke Tanaka ; Masahito Watanabe ; Kodai Ishibashi ; Hiroshi Matsuyama ; Yoko Saikawa ; Masaya Nakata
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：April 16, 2010
• 年：2010
• 卷：12
• 期：8
• 页码：1700-1703
• 全文大小：265K
• 年卷期：v.12,no.8(April 16, 2010)
• ISSN：1523-7052

文摘

One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dtz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.