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Synthesis 1991; 1991(5): 371-374
DOI: 10.1055/s-1991-26468
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Intramolecular Addition of Hydroxy Group to a Diene System: Oxymercuration - Demercuration and Titanium Tetrachloride Catalyzed Synthesis of Manoyl Oxides

Yolanda Amate* , Andrés García-Granados, Francisco A. López, Antonio Sáenz de Buruaga
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, E-18071 Granada, Spain
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Publication Date:
29 April 2002 (online)

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The stereochemistry of the formation of tetrahydropyran ring of ent-manoyl oxides from ent-8α-hydroxylabda-13(16), 14-dienes has been studied in one and two-step oxymercuration-demercuration (OM-DM) processes as well as by a new titanium tetrachloride catalyzed cyclization which allows the preparation of this tetrahydropyran moiety of C-13 epimer manoyl oxides in high yield.