ChemInform Abstract: A Highly Efficient and Shortcut Synthesis of Cyclitol Derivatives via Spiro Sugar Orthoesters.
Abstract
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ChemInform Abstract
Key steps of the novel synthesis of cyclitol derivatives (VI) are (a) the formation of enol ethers (V) by chemoselective pyran ring opening of sugar ortho esters (III) with methyl anions generated from AlMe3 and (b) the ZnCl2-catalyzed aldol cyclization of keto compounds (VII) in situ generated by DMSO oxidation of compounds (V). The cyclization proceeds with high to excellent diastereoselectivity.
