It is shown that the stereochemistry of addition reactions to 3-arylidene lactones (3) and (9) is controlled by the 5- rather than the 4-substituent: synthesis of the 2,3-trans 3,4-cis lignan dihydrosesamin (11) thus requires use of the 4,5-cis lactone (8), with epimerisation at C-2 following establishment of 3,4-cis geometry.
D. R. Stevens and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1990, 425 DOI: 10.1039/P19900000425
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