It is shown that the stereochemistry of additions to the 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 11b(R = H) thus requires use of the 4,5-cis- lactone 8, in the sequence 8(R1= TBDMS, R2= TMS)→9b→10b→11b(R = H), with epimerisation at C-2 following establishment of cis,cis geometry.
D. R. Stevens and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1992, 633 DOI: 10.1039/P19920000633
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