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Synlett 2001; 2001(1): 0153-0155
DOI: 10.1055/s-2001-9723
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Prehispanolone Analogs: Stereochemistry Control at C-5 in the Preparation of 1-Oxaspiro[4,5]decane Fused Systems and Related Compounds

Pilar Basabe* , Antonio Estrella, Isidro S. Marcos, David Díez, Anna M. Lithgow, A. J. P. White, David J. Williams, Julio G. Urones
  • *Dpto. de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain; Fax 00 34 923 29 44 82; E-mail: jgu@gugu.usal.es
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Publication Date:
31 December 2001 (online)

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A new strategy for acid-catalyzed intramolecular epoxide ring-opening is described for preparing grindelic acid derivatives. Proper functionalization of ring B allows stereochemical control for the epoxide and spiran carbons. The carbonyl group at C-7 allows the control of C-8 in the synthesis of prehispanolone analogues.

prehispanolone - spirolabdanes - terpenoids - cyclization

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