Summary
Ethylα-bromovinylacetate (VII) was condensed with the sodio derivative of ethyl piperonoylacetate (VIII) to give diethylα-vinyl-α′-piperonoylsuccinate (IX). The latter on reduction with lithium aluminium hydride furnished the triol (X), which underwent smooth cyclisation with 1% ethanolic hydrogen chloride to 2-(3′, 4′-methylenedioxyphenyl)-hydroxymethyl-4-vinyltetrahydrofuran (XIa). The structure of XIa was established by Oppenauer oxidation to an aldehyde. Ozonolysis of XIa afforded samin (I).
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Banerjee, D.K., Bhute, R.S. & Murty, N.L.N. Synthetic investigations in the sesamin group. Proc. Indian Acad. Sci. 58, 153–160 (1963). https://doi.org/10.1007/BF03049425
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DOI: https://doi.org/10.1007/BF03049425