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Synlett 1998; 1998(7): 693-699
DOI: 10.1055/s-1998-1754
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Carbocycles from Carbohydrates via Free Radical Cyclizations: Synthesis and Manipulation of Annulated Furanoses

José Marco-Contelles* , Carolina Alhambra, Angeles Martínez-Grau
  • *Instituto de Química Orgánica General (CSIC); Juan de la Cieva, 3; 28006-Madrid, Spain; Fax (91) 5 64-48 53; E-mail: iqmc21@pinar1.csic.es
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Publication Date:
31 December 2000 (online)

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Tributyltin hydride plus AIBN mediated free radical cyclization of chiral precursors derived from O-glycosylated carbohydrates is an efficient method for the asymmetric synthesis of carbocycles (cyclitols, aminocyclitols and pseudosugars) of biological and pharmacological interest. Starting from simple aldoses and after a series of trivial synthetic steps for hydroxyl protection and functionalization, it is possible to prepare the required radical precursor in the furanose form with a radical donor and acceptor at the appropriate positions. Under typical free radical cyclization conditions the desired annulated furanoses were obtained in good chemical yield and excellent acyclic diastereoselection at "off-template" sites. A large number of precursors have been synthesized and cyclized in order to analyze the scope and extent of this new synthetic methodology.

annulated furanoses - radical cyclization - carbohydrates - carbocycles - tin hydride

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