Unified strategy for the synthesis of the "Miscellaneous" lycopodium alkaloids:: Total synthesis of (±)-lyconadin A
Unified strategy for the synthesis of the "Miscellaneous" lycopodium alkaloids:: Total synthesis of (±)-lyconadin A
复制标题
DOI：
10.1021/ja8028069
复制
发表时间：
2008-06-11
影响因子：
15
通讯作者：
Sarpong, Richmond
中科院分区：
文献类型：
--
作者：
Bisai, Alakesh;West, Scott P.;Sarpong, Richmond
石松属生物碱lyconadin A的全合成从一个容易获得的乙烯基酯和溴甲基吡啶开始，在18个步骤中实现。全合成中的关键步骤是由四环前体产生的邻近驱动的氧化C-N键形成反应。首次合成的关键化合物四环素是一种多用途的中间体，可用于石松生物碱的全合成。该计划成功的关键是吡啶环化环庚三烯的有效制备，这有望成为获得各种含七元环的天然产物的一般策略。
Total synthesis of the Lycopodium alkaloid lyconadin A was achieved in 18 steps starting from a readily available vinylogous ester and bromopicoline. The key step in the total synthesis is a proximity-driven oxidative C-N bond-forming reaction that yields the lyconadin pentacycle from a tetracyclic precursor. The key tetracycle, which has been prepared for the first time, is a versatile intermediate that may be utilized for the total synthesis of a variety of Lycopodium alkaloids. Critical to the success of this plan was the efficient preparation of a pyridine-annulated cycloheptadiene tricycle that promises to be a general strategy to access a variety of seven-membered ring containing natural products.