Tetrahedron Letters p. 745 - 748 (1994)
Update date:2022-07-29
Topics:
Murakami, Teiichi
Minamikawa, Hiroyuki
Hato, Masakatsu
D-erythro-Sphingosine (1) and phytosphingosine (2) have been efficiently synthesized from D-glucosamine by utilizing its whole carbon skeleton and functional groups. In this synthetic route, regioselective alkylation of the epoxy-tosylate 9 was achieved with a copper(I)-catalyzed Grignard reagent to give the key intermediate 10, which was converted to both 1 and 2 via regioselective formation of the iodohydrin 11.
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