Synthesis of a (4E, 8Z)-Sphingadienine Moiety Containing Cerebroside fromTetragonia Tetragonoideswith Antiulcerogenic Activity1,2

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Abstract
The natural cerebroside 1a possessing antiulcerogenic activity and its diastereomer 1b were readily synthesized via the azidosphingosine glycosylation method. The required (4E, 8Z) - azidosphingadienine 13 was obtained from (4Z)-tetradecenyl bromide (8) and 2,4-O-benzylidene-D-threose (10) via Wittig reaction, subsequent azide introduction and benzylidene group removal. For the glucosylation the 3-O-benzoyl derivative 16 was prepared; it provided, with the O-(tetra-O-acetyl-β-D-glucopyranosyl)trichloroacetimidate (17), the desired O-glucosyl derivative 18 in high yield. Deprotection and azido group reduction afforded compound 20 with a free amino group. N-Acylation with both enantiomers of α-hydroxy palmitic acid (using the derivatives 21a,b) yielded, after deacylation, compounds 1a and 1b, respectively.