Chemistry - A European Journal p. 1915 - 1921 (2011)
Update date:2022-07-30
Topics:
Berhal, Farouk
Takechi, Sho
Kumagai, Naoya
Shibasaki, Masakatsu
In an attempt to explore the synthetic utility of a ternary asymmetric catalyst comprising La(NO3)3·6H2O, amide-based ligand (R)-L1, and D-valine tert-butyl ester H-D-Val-OtBu, we investigated a catalytic, asymmetric amination of functionalized N-nonsubstituted α-alkoxycarbonyl amides using di-tert-butyl azodicarboxylate as an electrophilic aminating reagent. A highly functionalized, cyclic N-nonsubstituted α-alkoxycarbonyl amide delivered the desired amination product in up to 96% enantiometric excess, with the requisite functionalities of the polar heads of sphingosines with the appropriate stereochemical arrangement. The rapid asymmetric assembly of these functional groups allowed a concise enantioselective synthetic route to sphingosines to be established with a broad flexibility towards derivative synthesis. These studies have culminated in an efficient catalytic enantioselective total synthesis of immunosuppressive fungal metabolites mycestericina F (3a) and G (3b).
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Doi:10.1016/j.jorganchem.2008.09.030
(2008)Doi:10.1007/s00706-007-0802-3
(2008)Doi:10.1055/s-0028-1083143
(2008)Doi:10.1002/bscb.19860950905
(1986)Doi:10.1002/ardp.19592921112
(1959)Doi:10.1016/0022-328X(86)80362-X
(1986)