3 years ago

Carbene-Catalyzed Formal [5 + 5] Reaction for Coumarin Construction and Total Synthesis of Defucogilvocarcins

Carbene-Catalyzed Formal [5 + 5] Reaction for Coumarin Construction and Total Synthesis of Defucogilvocarcins
Yonggui Robin Chi, Zhichao Jin, Giuseppe Zanoni, Zhijian Huang, Xuan Huang, Yuexia Zhang, Tingshun Zhu
An N-heterocyclic carbene-catalyzed formal [5 + 5] reaction between enals and furanones that generates multisubstituted coumarins in a single step is reported. Five atoms in each of the substrates are involved in this catalytic process to form a benzene and a lactone ring. The power of the method is further demonstrated in metal-free total syntheses of several natural products (defucogilvocarcins M, E, and V) bearing coumarin as the key structural motif.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03102

DOI: 10.1021/acs.orglett.7b03102

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