Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core.
Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core.
复制标题
DOI：
10.1021/jacs.5b05205
复制
发表时间：
2015-07-01
影响因子：
15
通讯作者：
Larionov OV
中科院分区：
文献类型：
--
作者：
Mfuh AM;Zhang Y;Stephens DE;Vo AX;Arman HD;Larionov OV
我们报道了一种简便有效的构建顺-1，2-恶唑卡林体系的方法，该体系区别于(前)毛霉胺、曲霉素A、格列韦林和FA-2097。1，2-恶唑杂环的形成是通过αC-锂的O-硅基丙酮酸乙酯与苯醌的1，2-加成反应完成的，然后是氧-迈克尔环的闭合。该方法成功地用于简明全合成毛霉胺A(克量)、毛霉胺B，以及首次合成毛霉胺C。
We report herein a facile and efficient method of the construction of the cis-1,2-oxazadecaline system, distinctive of (pre)trichodermamides, aspergillazine A, gliovirin and FA-2097. The formation of the 1,2-oxazadecaline core was accomplished by a 1,2-addition of an αC-lithiated O-silyl ethyl pyruvate oxime to benzoquinone, that is followed by an oxa-Michael ring-closure. The method was successfully applied to the concise total synthesis of trichodermamide A (in gram quantities), trichodermamide B, as well as the first synthesis of trichodermamide C.