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Title: Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins
Authors: Huang, Xuan
Zhu, Tingshun
Huang, Zhijian
Zhang, Yuexia
Jin, Zhichao
Zanoni, Giuseppe
Chi, Robin Yonggui
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2017
Source: Huang, X., Zhu, T., Huang, Z., Zhang, Y., Jin, Z., Zanoni, G., & Chi, R. Y. (2017). Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins. Organic letters, 19(22), 6188-6191. doi:10.1021/acs.orglett.7b03102
Journal: Organic letters
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.
ISSN: 1523-7060
DOI: 10.1021/acs.orglett.7b03102
Rights: © 2017 American Chemical Society. All rights reserved. This paper was published in Organic letters and is made available with permission of American Chemical Society.
Fulltext Permission: open
Fulltext Availability: With Fulltext
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