Journal of the Chemical Society. Perkin transactions I p. 2849 - 2858 (1994)
Update date:2022-08-05
Topics:
Nakashima, Hideki
Hirata, Norihiko
Iwamura, Takeru
Yamagiwa, Yoshiro
Kamikawa, Tadao
(2S,3S,4R)-2-<(2'R)-2-Benzoyloxydocosanoylamino>-16-methylheptadecane-1,3,4-triol 3,4-dibenzoate 32, apertially protected ceramide part of a cerebroside from the marine sponge Halichondria japonica, has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined.The key steps in the synthesis include the regioselective ring opening of chiral epoxide 5 with a 2-alkyl-2-lithio-1,3-dithiane and the introduction of a hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality.
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