Abstract
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 1 O 2 to the double bond, which is important for the mechanism of such reactions.
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