Total synthesis of flustramine C via dimethylallyl rearrangement
Total synthesis of flustramine C via dimethylallyl rearrangement
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DOI：
10.1021/ol0627348
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发表时间：
2007-01-18
期刊：
影响因子：
5.2
通讯作者：
Boehrer, Petra
中科院分区：
文献类型：
--
作者：
Lindel, Thomas;Braeuchle, Laura;Boehrer, Petra
[图解]以N-b-甲基色胺为起始原料，经五步反应合成了来自苔藓虫Flustra foliacea的海洋天然产物氟胺C，产率为38%。关键步骤是天然产物deformylflustrobromide的仿生氧化，导致反异戊二烯基的选择性1，2-重排。通过H-1，N-15 HMBC实验，明确表明与t-BuOCl的反应始于侧链氮的氯化。脱甲酰基氟溴本身通过Danishefsky反异戊二烯化反应合成。
[GRAPHIC]The marine natural product flustramine C from the bryozoan Flustra foliacea was synthesized in five steps and 38% yield starting from N-b-methyltryptamine. The key step is the biomimetic oxidation of the natural product deformylflustrabromine causing selective 1,2-rearrangement of the inverse prenyl group. By H-1,N-15 HMBC experiments, it is unambiguously shown that the reaction with t-BuOCl commences with chlorination of the side chain nitrogen. Deformylflustrabromine itself was synthesized via Danishefsky inverse prenylation.