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Synlett 1995; 1995(7): 776-778
DOI: 10.1055/s-1995-5050
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Asymmetric Induction in Intramolecular [2+2] Photocycloaddition of Alkyl Hex-2-enopyranosid-4-uloses and Further Transformations of the Cycloadducts

Alphonse Tenaglia* , Delphine Barillé
  • *Réactivité en Synthèse Organique, URA CNRS 1411, Faculté de St Jérôme, Av. Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France, Fax 91 28 88 41
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Publikationsdatum:
31. Dezember 2000 (online)

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An efficient intramolecular [2+2] photocycloaddition of alkyl hex-2-enopyranosid-4-uloses allows the construction of two new cyclic systems annelated to the pyranoside moiety with stereocontrol of 3 or 4 carbogenic centers. The regioselective ring cleavage of the cycloadducts affording new bicyclic pyranoid compounds is described.

Alkyl Hex-2-enopyranosid-4-uloses - intramolecular [2+2] photocycloaddition - regioselective ring cleavage - pyranoids