American Chemical Society
Browse
ol7b03102_si_001.pdf (4.73 MB)

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

Download (4.73 MB)
journal contribution
posted on 2017-11-06, 14:23 authored by Xuan Huang, Tingshun Zhu, Zhijian Huang, Yuexia Zhang, Zhichao Jin, Giuseppe Zanoni, Yonggui Robin Chi
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.

History