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Synthesis 1997; 1997(12): 1415-1419
DOI: 10.1055/s-1997-1361
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Hydroxylated α-Vinylpyrrolidines from Sugar-Derived 2,5-Dihydrofurans. Synthesis of (1S,2S,8aR)-1,2-Dihydroxyindolizidine by Ring Closing Olefin Metathesis

Claudio Paolucci* , Lorenzo Musiani, Francesca Venturelli, Antonino Fava
  • *Dipartimento de Chimica Organica “A. Mangini”-Università di Bologna, Viale Risorgimento, 4, I-40136 Bologna, Italy, Fax +39(51)644-3654; E-mail: fava@antlab.cineca.it
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Publication Date:
31 December 2000 (online)

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Sugar-derived dihydrofurans carrying an amino function at the terminus of a two-carbon branch undergo Hg(II)-promoted cyclization to give mercury substituted oxa-aza bicyclic compounds. Thiol promoted deoxymercuration results in cleavage of the tetrahydrofuran ring and formation of hydroxylated 2-vinylpyrrolidines. These appear to be convenient precursors for the synthesis of indolizidines via ring-closing olefin metathesis. As an example the synthesis of a new lentiginosine epimer is reported.

dihydrofurans - hydroxylated pyrrolidines - indolizidines - azasugars - ring closing olefin metathesis