3 years ago

Synthesis and Configuration of Neomaclafungin A

Synthesis and Configuration of Neomaclafungin A
Shijun Zhu, Yikang Wu
The relative and absolute configuration of neomaclafungins were impossible to establish by spectroscopic analyses alone because of the lack of exploitable 1H-1H couplings and nOes between the upper and the lower subunits. This very difficult task now is finally completed by an enantioselective total synthesis of neomaclafungin A (revised) and its diastereomer (reported). The results also provided a key reference for the complete structures for other neomaclafungins and the long-known closely related natural product maclafungin. Although the relative configurations of the upper and lower fragments of neomaclafungin A were assigned, establishment of the configuration for the whole molecule remained impossible because of the lack of exploitable 1H-1H couplings between the two fragments. Now the problem has been solved by an enantioselective total synthesis. Some interesting relative configuration-dependent reactivity differences were also observed en route to the total synthesis.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201700950

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