Journal of Organic Chemistry p. 4773 - 4779 (1988)
Update date:2022-08-03
Topics:
Knapp, Spencer
Levorse, Anthony T.
Potenza, Joseph A.
The synthesis of the title compound from the Diels-Alder adduct of diethyl ketomalonate and 1,3-butadiene (nine steps, 13percent overall yield) is described.The key step is a transannular "bromolactamization" reaction, which sets up the stereocontrolled functionalization of the pyran ring.The use of resolved p-methoxyenethylamine as the source of the amino group allows the synthesis of both the D (natural) and L (unnatural) series amino sugars.
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(1988)
