Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis. Chen, V. Y. & Kwon, O. Angewandte Chemie International Edition, 60(16):8874–8881, April, 2021.
Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis [link]Paper  doi  abstract   bibtex   
Abstract Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non‐trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine‐palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
@article{chen_unified_2021,
	title = {Unified {Approach} to {Furan} {Natural} {Products} via {Phosphine}‐{Palladium} {Catalysis}},
	volume = {60},
	issn = {1433-7851, 1521-3773},
	url = {https://onlinelibrary.wiley.com/doi/10.1002/anie.202015232},
	doi = {10.1002/anie.202015232},
	abstract = {Abstract 
            Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non‐trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine‐palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.},
	language = {en},
	number = {16},
	urldate = {2024-10-25},
	journal = {Angewandte Chemie International Edition},
	author = {Chen, Violet Yijang and Kwon, Ohyun},
	month = apr,
	year = {2021},
	pages = {8874--8881},
}

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