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Issue 7, 1995
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Radical cyclisation route to furanolignans: short and stereoselective synthesis of (±)-dihydrosesamin and (±)-lariciresinol

Abstract

The furanolignans, (±)-dihydrosesamin 3a and (±)-lariciresinol 4 have been synthesised by a very short and stereoselective route in good overall yield using a radical cyclisation as the key step. The radical precursor 2, prepared from the easily accessible cinammyl alcohol 1, on radical cyclisation in the presence of Bu3SnH and a catalytic amount of AIBN, furnished 3 along with a second isomer in a ratio of 7:1. The product 3a was identical with natural dihydrosesamin. The lariciresinol dibenzyl ether 3b, on controlled catalytic hydrogenation, afforded (±)-lariciresinol 4 in excellent yield.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1995, 927-929
Article type
Paper

Radical cyclisation route to furanolignans: short and stereoselective synthesis of (±)-dihydrosesamin and (±)-lariciresinol

G. Maiti, S. Adhikari and S. C. Roy, J. Chem. Soc., Perkin Trans. 1, 1995, 927
DOI: 10.1039/P19950000927

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