![[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-(2,2,2-trichloroethoxycarbonyloxy)propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate structure](https://static.chemtradehub.com/structs/100/100431-55-8-7104.webp "[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-(2,2,2-trichloroethoxycarbonyloxy)propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate structure")
Synthesis of 2-chromanone-fused [3.2.0] bicycles through a phosphine-mediated tandem [3 + 2] cyclization/intramolecular Wittig reaction
Literature Information
Publication Date
2021-09-15
DOI
10.1039/D1QO01013A
Impact Factor
5.281
Authors
Junfeng Fu, Ingrid Rakielle Tsapy Takia, Peng Chen, Wei Liu, Chengjun Jiang, Weijun Yao, Xiaofei Zeng, Yongjiang Wang, Xiaoyu Han
View Original
Abstract
A phosphine-mediated tandem [3 + 2] cyclization/intramolecular Wittig reaction of 3-aroylcoumarin with alkynone is described. The high efficiency of the tandem process allows the synthesis of 2-chromanone-fused bicyclo[3.2.0]heptenones in moderate to high yields with remarkably high regio- and diastereoselectivities under mild reaction conditions, which represents an extremely simple, economical and straightforward synthetic method to construct complex cyclic building blocks with potential biological applications.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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(2E)-3-(3-Chlorophenyl)-N-{2-[4-(methylsulfonyl)-1-piperazinyl]-2-oxoethyl}acrylamide
CAS Number:
2505001-54-5
Molecular Formula:
C16H20ClN3O4S
4-Methyl-3-morpholinecarboxylic acid hydrochloride (1:1)
CAS Number:
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Molecular Formula:
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