Total synthesis of diazonamide A.
Total synthesis of diazonamide A.
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DOI：
10.1039/c0sc00577k
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发表时间：
2011
期刊：
影响因子：
8.4
通讯作者：
Macmillan DW
中科院分区：
文献类型：
--
作者：
Knowles RR;Carpenter J;Blakey SB;Kayano A;Mangion IK;Sinz CJ;Macmillan DW
完成了海洋天然产物重氮酰胺A(1)的全合成。这项工作的特点是高度立体选择性地合成了C(10)四元中心和中心呋喃吲哚中心，这是通过亚胺催化的烷基化-环化级联反应实现的。此外，开发了镁介导的分子内大醛化反应和钯催化的串联硼化/环化反应，以关闭重氮酰胺A的两个12元大环。该合成包括最长线性序列的20个步骤，总收率为1.8%。
A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation–cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation were developed to enable the closure of the two 12-membered macrocycles of diazonamide A. This synthesis involves 20 steps in its longest linear sequence and proceeds in 1.8% overall yield.