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

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...

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Bibliographic Details
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
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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