α-Hydroxyalkylation of β-(3,4-methylenedioxybenzyl)-γ-butyrolactone (1) with 3,4,5-trimethoxybenzaldehyde, using lithium hexamethyldisilylamide as a base, affords a 1 : 1 mixture of (±)-podorhizol (4) and (±)-epipodorhizol (5); Jones's oxidation of this mixture gives (±)-podorhizone (6) in 63% overall yield.
E. Brown, J. Robin and R. Dhal, J. Chem. Soc., Chem. Commun., 1978, 556 DOI: 10.1039/C39780000556
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