Investigation of a Domino Heck Reaction for the Rapid Synthesis of Bicyclic Natural Products

(Figure Presented) Unexpected Heck: During efforts toward the synthesis of FR900482, an unexpected domino Heck product was isolated (see scheme). Although this pathway was ultimately not productive for the aforementioned natural product synthesis, efforts were made to extend the methodology to the synthesis of amurensinine. To our knowledge this domino reaction was the first such tandem Heck-alkylation pathway in the presence of a geometrically favorable β-hydrogen elimination. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.