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

Xuan Huang; Tingshun Zhu; Zhijian Huang; Yuexia Zhang; Zhichao Jin; Giuseppe Zanoni; Yonggui Robin Chi

doi:10.1021/acs.orglett.7b03102

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

Xuan Huang, Tingshun Zhu, Zhijian Huang, Yuexia Zhang, Zhichao Jin, Giuseppe Zanoni, Yonggui Robin Chi^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	6188-6191
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.7b03102
Publication status	Published - Nov 17 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "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.",

author = "Xuan Huang and Tingshun Zhu and Zhijian Huang and Yuexia Zhang and Zhichao Jin and Giuseppe Zanoni and Chi, {Yonggui Robin}",

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AU - Huang, Xuan

AU - Zhu, Tingshun

AU - Huang, Zhijian

AU - Zhang, Yuexia

AU - Jin, Zhichao

AU - Zanoni, Giuseppe

AU - Chi, Yonggui Robin

PY - 2017/11/17

Y1 - 2017/11/17

N2 - 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.

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

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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