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Issue 19, 1994
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Total synthesis of (2S,3S,4R)-2-[(2′R)-2-benzoyloxydocosanoylamino]-16-methylheptadecane-1,3,4,-triol 3,4-dibenzoate, a partially protected ceramide part of sponge cerebrosides

Abstract

(2S,3S,4R)-2-[(2′R)-2-Benzoyloxydocosanoylamino]-16-methylheptadecane-1,3,4-triol 3,4-dibenzoate 32, a partially 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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Article information


J. Chem. Soc., Perkin Trans. 1, 1994, 2849-2857
Article type
Paper

Total synthesis of (2S,3S,4R)-2-[(2′R)-2-benzoyloxydocosanoylamino]-16-methylheptadecane-1,3,4,-triol 3,4-dibenzoate, a partially protected ceramide part of sponge cerebrosides

H. Nakashima, N. Hirata, T. Iwamura, Y. Yamagiwa and T. Kamikawa, J. Chem. Soc., Perkin Trans. 1, 1994, 2849
DOI: 10.1039/P19940002849

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