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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Doi:10.1016/j.bmc.2011.04.014
(2011)Doi:10.1021/acsmedchemlett.0c00194
(2020)Doi:10.1016/S0040-4020(01)90308-4
(1987)Doi:10.1021/ja01122a084
(1952)Doi:10.1055/s-0040-1706599
(2021)Doi:10.1246/cl.1988.59
(1988)
