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Synlett 1997; 1997(5): 627-628
DOI: 10.1055/s-1997-3219
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Stereoselective Synthesis of cis-2,5-Disubstituted Tetrahydrofurans: An Approach to Pamamycins

Luca Arista1 , Michelangelo Gruttadauria1 , Eric J. Thomas2
  • 1Dipartimento di Chimica Organica “E. Paternò”, Università di Palermo, Via Archirafi No. 20, 90123 Palermo, Italy
  • 2Department of Chemistry, University of Manchester, Manchester M13 9PL, U.K.
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Publikationsdatum:
31. Dezember 2000 (online)

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A stereoselective synthesis of 2,5-cis-disubstituted tetrahydrofurans has been devised based on the epoxidation and rearrangement of products prepared from aldehydes with remote induction using allylstannanes and tin(IV) halides. This chemistry has been applied to synthesize the tetrahydrofuran containing fragments of (-)-nonactic acid and the pamamycins.

allylstannane - remote induction - tetrahydrofuran - selenide

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