Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins

• Main Authors: Huang, Xuan, Zhu, Tingshun, Huang, Zhijian, Zhang, Yuexia, Jin, Zhichao, Zanoni, Giuseppe, Chi, Robin Yonggui
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry::Organic chemistry; Chemical Response; Aromatic Compounds
• Online Access: https://hdl.handle.net/10356/138310
• Institution: Nanyang Technological University

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.