Synthesis p. 3693 - 3699 (2010)
Update date:2022-07-30
Topics:
Baskakova, Alevtina
Frey, Wolfgang
Jaeger, Volker
In contrast to amino acids with a bulky substituent like tert-leucine, adamantylglycine has so far received little attention. Here, a new, practical synthesis of adamantylglycine is described. This is based on a highly diastereoselective addition of adamantyl Grignard reagent to 2,3-O-cyclohexylideneglyceraldehyde N-benzylnitrone, mediated by the Lewis acid diethylaluminum chloride. Adamantylglycine is obtained from the nitrone in 6 steps and 28% yield as a crystalline hydrochloride with 0.5 methanol incorporated.
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Doi:10.2174/157340610793563992
(2010)Doi:10.1039/c7cc05225a
(2017)Doi:10.1016/j.chembiol.2020.11.004
(2021)Doi:10.1055/s-0030-1258238
(2010)Doi:10.1016/j.bmc.2010.11.007
(2011)Doi:10.1016/j.tetasy.2010.10.012
(2010)