Intramolecular 1,5- versus 1,6-hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrate models

3 pages, 1 table, 2 schemes.-- PMID: 12027657 [PubMed].-- Printed version published May 30, 2002.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/ol025981uErratum to this paper published in: Org. Lett. 4(19): 3337 (2002), http://dx.doi.org/10.1021/ol020134cThe alkoxy radical generated by reaction of 3,7-anhydro-2-deoxyoctitols with (diacetoxyiodo)benzene (DIB) and iodine abstracts regioselectively either the proton at C7 or that at C4 depending on the electronegativity of the substituent at C4. The correct election of this substituent can switch the reaction to give 2,9-dioxabicyclo[3.3.1]nonane or hexahydro-2H-furo[3,2-b]pyran ring systems.This work was supported by the Investigation Programs BQU2000-0650 and BQU2001-1665 of the Dirección General de Investigación Científica y Técnica, Spain. A.J.H. and I.P.-M. thank the Ministerio de Educación y Ciencia, Spain, and the Program I3P-CSIC, respectively, for fellowships