4.8 Article

Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 16, Pages 8874-8881

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202015232

Keywords

furan natural products; furan synthesis; Heck reaction; Michael addition; phosphine– palladium catalysis

Funding

  1. NIH [R01GM071779]

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This paper presents a general synthetic protocol for polyalkyl furans using a Michael-Heck approach with sequential phosphine-palladium catalysis. The versatility of this method is demonstrated through the total syntheses of nine distinct polyalkylated furan natural products from readily available precursors.
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.

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