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Synlett 1993; 1993(10): 785-787
DOI: 10.1055/s-1993-22609
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Diastereodivergent Formation of 2,3-trans:3,4-cis- and 2,3-cis:3,4-trans-2,3,4-Trisubstituted Tetrahydrofurans from the Common 2,5-Disubstituted-4,5-dihydro-1,3-dioxepin: A Diastereocontrolled Route to Furofuran Lignan (±)-Asarinin

Seiichi Takano* , Kiyohiro Samizu, Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan
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Publication History

Publication Date:
19 March 2002 (online)

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Both 2,3-trans:3,4-cis- and 2,3-cis:3,4-trans-2,3,4-trisubstituted tetrahydrofurans can be generated in diastereoselective manners from the common 2,5-disubstituted-4,5-dihydro-1,3-dioxepin by selecting appropriate acid conditions. Exploiting the present finding diastereoselective route to a furofuran lignan (±)-asarinin has been developed.

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