Abstract

The transacetalization of 1,1,3,3-tetramethoxypropane and an N-benzoylaminodiol provided stereoselectively the corresponding 2,5-disubstituted-1,3-dioxanes. The stereochemistry of the rings formed in the transacetalization depended on the structure of the amino diol, and the ratio of the products depended on the reaction conditions, as expected. This kind of stereoselective transacetalization not only gives a series of useful building blocks but also generates interesting 1,3-dioxanes which target protein kinase C.

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