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Synlett 2001; 2001(3): 0400-0402
DOI: 10.1055/s-2001-11419
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Asymmetric Syntheses of Trisubstituted Tetrahydrofuran Lignans, Sesaminone and 4-Epidihydrosesamin

Hidemi Yoda* , Kohei Kimura, Kunihiko Takabe
  • *Department of Molecular Science, Faculty of Engineering, Shizuoka University, Hamamatsu 432-8561, Japan; Tel/Fax + 81(53)4 78 11 50; E-mail: yoda@mat.eng.shizuoka.ac.jp
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Publication Date:
31 December 2001 (online)

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An efficient and stereodefined process is described for the preparation of 2,3,4-trisubstituted tetrahydrofuran lignans, sesaminone and 4-epidihydrosesamin. The synthetic strategy is based on the similar chemoselective hydrogenation of functionalized lactol derivatives, elaborated through asymmetric condensation of a 4,5-trans-disubstituted lactone.

sesaminone - dihydrosesamin - lignan - chemoselective deoxygenation - trisubstituted γ-lactone