The carbohydrate α-enone (1) condenses with butadiene in the presence of an excess of aluminium chloride to give the lyxo adduct (2), exclusively, reduction of which is also stereospecific; a method has been developed to convert the product into the cyclopentanofuranoside (7).
J. L. Primeau, R. C. Anderson and B. Fraser-Reid, J. Chem. Soc., Chem. Commun., 1980, 6 DOI: 10.1039/C39800000006
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