Thermal treatment of the o-hydroxymethylbenzylsilane (3) with an excess of maleic anhydride yielded the 1,2,3-trisubstituted tetrahydronaphthalene (8) with a cis configuration, via the benzyl equivalent of the Peterson reaction, which was converted stereoselectively into (±)-deoxypodophyllotoxin (13) in good overall yield via a regio- and stereo-selective sequence of reactions.
S. Takano, S. Otaki and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1985, 485 DOI: 10.1039/C39850000485
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