A Novel Approach Towards Dibenzylbutyrolactone Lignans Involving Heck and Radical Reactions: Application to (±)‐Matairesinol Synthesis

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A highly regio‐ and stereoselective Heck reaction of iodoarenes with vinylated malonates, generated in situ by fluoride‐induced protiodesilylation of alkenylsilanols/disiloxanes to give functionalized styrenes and 1,4‐diaryl‐1‐butenes has been developed. The dibenzylbutyrolactone lignan skeletons have been achieved from 1,4‐diaryl‐1‐butenes by two routes involving diastereoselective radical cyclization as the key step. This strategy has successfully been applied in the synthesis of (±)‐matairesinol.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)