Tetrahedron p. 917 - 922 (1986)
Update date:2022-08-03
Topics:
Cardillo
Orena
Sandri
Tomasini
A stereoselective synthesis of (±)-erythro-sphingosine triacetate (1) is described. The key reaction that determines the right stereochemistry is the iodocyclization of 1-trichloroacetimido-(2E,4E)-octadecadiene (5). The 4,5-dihydro-1,3-oxazine (6) through cleavage with HCl and treatment with Amberlyst A 26 in the AcO- form, followed by full acetylation, affords (1) in good yield.
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Doi:10.1016/S0040-4039(01)98800-8
(1968)Doi:10.1016/S0277-5387(96)00405-6
(1997)Doi:10.1080/00397919708006049
(1997)Doi:10.1016/S0040-4039(00)73340-5
(1994)Doi:10.1039/a607668h
(1997)Doi:10.1002/hc.10190
(2003)
