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2005
Lipids
U 0750
20- 209
Cross Metathesis Route in Sphingomyelin Synthesis. — A new route for the synthesis of sphingomyelin (IX), an important substance in maintaining the microdomain
structure in cell membranes, is presented. Cross metathesis reaction of the N-Boc alcohol (I) using Grubbs' second generation catalyst proceeds stereoselectively to afford
Boc sphingosine (III) in good yield. The synthesis of the targeted sphingomyelin is then
achieved via a selective phosphorylation reaction followed by acylation of the amino
group and substitution of the alkyl bromide by NMe3. The conditions for the cross-metathesis reaction are optimized with the help of different model compounds. —
(HASEGAWA, H.; YAMAMOTO, T.; HATANO, S.; HAKOGI, T.; KATSUMURA*,
S.; Chem. Lett. 33 (2004) 12, 1592-1593; Sch. Sci. Technol., Kwansei Gakuin Univ.,
Sanda, Hyogo 669, Japan; Eng.) — H. Haber
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