Abstract
Reactions of ortho esters of myo-inositol 8 or 10 with 1-2 equiv of Grignard reagents in benzene-ether yield regio- and stereoselectively the corresponding ring opening products having a free hydroxy group at C-1. The regioselectivity is rationalized owing to the presence of the 2-methoxy group which will serve as an auxiliary to form a chelation complex 12 with magnesium. Inositol derivatives having two free hydroxy group at C-1 and C-3 positions can be achieved from reactions of 6 or 8 with excess Grignard reagents or under more drastic conditions. The reaction of 8b with excess LiAlH(4)/AlCl(3), on the other hand, yields the corresponding 1,5-diol 19.
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