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A convenient synthesis of a racemic A-ring precursor of dihydroxyvitamin D-3 (calcitriol) is described. The key step involves the singlet oxygen ene reaction of the Lythgoe lactone, which proceeds with excellent regio- and good diastereoselectivities. Strong polar interactions are operative during the attack of O-1(2) to the double bond, which is important for the mechanism of such reactions
An acyclic alkene derived from a carbohydrate is employed as a substrate for manganese-mediated radical reactions for the first time. The addition of malonate is interesting for the mechanism of such reactions, whereas acetic acid as radical precursor affords lactones in excellent yield. The main diastereomer was easily separated and represents a key intermediate in the synthesis of KDO