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9. In the conversion of 17 to 18 why does the acetal form between C2-C3 and C5-C6 rather than C4-C5 or C3-C4?


R. R. Gadikota et al. /Tetrahedr 우 rete- 유 Scheme 2 Regente
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Answer #1

If we look at the structure 18, the alcoholic OH is converted to ketone by the cyclic contraction process, a pinacol pinacolone rearrangement, by which the intermediate stereochemistry uneffected. In the next step obviously the hydroxyl groups are protected by acetals, where acetal formation takes place at C2-C3 and C5-C6.

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