Abstract
AbstractChiral, substituted 3‐formylfurans have found widespread applications as synthetic intermediates and are key structural motifs in a variety of bioactive natural products. However, methods for their preparation are scant. We report herein an efficient and general route to synthesize them from suitably protected 2‐iodoenones derived from glycals. The synthetic protocol involves Heck coupling between substituted 2‐iodoenones and olefins followed by N‐bromosuccinimide (NBS)‐mediated electrophilic cyclization sequence, using H2O as a nucleophile. Similarly, a fully substituted chiral 3‐formylfuran can be prepared utilizing a two‐step approach starting with β‐methylstyrene as an olefinic partner in the Heck coupling. Further, to demonstrate the potential of our method, we have synthesized a furo[3,2‐c]pyran derivative and a fully protected chiral furan.
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