Synthesis of the lignan (±)-dihydrosesamin: problems of stereocontrol in the formation of 2,3,4-trisubstituted tetrahydrofurans and tetrahydrofuranones
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 425-426
- https://doi.org/10.1039/p19900000425
Abstract
It is shown that the stereochemistry of addition reactions to 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 (11) thus requires use of the 4,5-cis lactone (8), with epimerisation at C-2 following establishment of 3,4-cis geometry.This publication has 11 references indexed in Scilit:
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