From Carbohydrates to Carbocycles: Radical Routes via Tellurium Derivatives

Article abstract of DOI:10.1016/S0040-4020(01)85616-7

D-Ribose was transformed to its protected tosylate 15, followed by a Wittig-reaction to give 16 as a 3:1 mixture of the corresponding Z and E isomers.This mixture was then transformed to the anisyltelluride 17 and the latter cyclized in a radical exchange reaction to a mixture of the carbocycles 18a and 18b (in a 17:2 ratio).The major product 18a was then transformed to various chiral cyclopentane derivatives including the cyclopentenone-derivative 23.Various other carbohydrate-based approaches have also been explored.