Proceedings of the Indian Academy of Sciences - Section A

, Volume 58, Issue 3, pp 153–160

Synthetic investigations in the sesamin group

Part I. Synthesis of samin, a degradation product of sesamolin
  • D. K. Banerjee
  • R. S. Bhute
  • N. L. N. Murty
Article

DOI: 10.1007/BF03049425

Cite this article as:
Banerjee, D.K., Bhute, R.S. & Murty, N.L.N. Proc. Indian Acad. Sci. (1963) 58: 153. doi:10.1007/BF03049425
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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).

Copyright information

© Indian Academy of Sciences 1963

Authors and Affiliations

  • D. K. Banerjee
    • 1
  • R. S. Bhute
    • 1
  • N. L. N. Murty
    • 1
  1. 1.Organic Chemistry DepartmentIndian Institute of ScienceBangalore