Didier Charles, Critcher Douglas J, Walshe Nigel D, Kojima Yasuhiro, Yamauchi Yuji, Barrett Anthony G M
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK.
J Org Chem. 2004 Nov 12;69(23):7875-9. doi: 10.1021/jo048711t.
The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.
通过X射线晶体学和以2-氯硝基苯为原料的部分合成，确定了不同寻常的驱虫性吡咯并苯并恶嗪类萜烯天然产物CJ-12662的结构。利用一种不同寻常的迈森海默型重排反应构建核心吡咯并苯并恶嗪杂环，并用四环吡咯并苯并恶嗪内酯与萜烯醇进行偶联反应完成了CJ-12662的合成。
