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Synlett 1995; 1995(8): 855-856
DOI: 10.1055/s-1995-5089
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Regio and Stereoselectivity in the Synthesis of a 2,2,6,6 Tetrasubstituted Tetrahydropyran from Geranyl Acetate. Synthesis of Dihydropyrans

Julio G. Urones* , David Díez, Isidro S. Marcos, Pilar Basabe, Narciso M. Garrido, Ricardo Escarcena, A. M. Lithgow, M. F. Dominguez, J. M. Sánchez
  • *Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain
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Publication Date:
31 December 2000 (online)

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The tetrahydropyranic fraction from the cyclization of geranyl acetate with phenylselenenic acid has only two racemic diastereoisomers that were separated as their hydroxyderivatives 7 and 8. The establishment of the stereochemistry for both pairs of diastereoisomers is reported as well as the transformation of 7 and 8 into a unique racemic dihydropyrane 4, a precursor of β-pyrones. A mechanism for the regio-stereoselective cyclization is proposed.

Cyclization - geranyl acetate - phenylselenenic acid - tetrahydropyranes - stereoselective synthesis - dihydropyranes - β-pyrones