Synthesis of a plasmenylethanolamine
Keyword(s):
One Pot
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Abstract A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an optically active known diol through eight steps. The key transformations for the synthesis of PlsEtn-[16:0/18:1 n-9] are, (1) regio- and Z-selective vinyl ether formation via alkylation of a lithioalkoxy allyl intermediate with an alkyl iodide, and (2) a one-pot phosphite esterification–oxidation sequence to construct the ethanolamine phosphonate moiety in the presence of the vinyl ether functionality. The piperidine salt of synthetic PlsEtn-[16:0/18:1 n-9] was desalinated through reversed-phase HPLC purification.
2008 ◽
Vol 31
(19)
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pp. 2988-3000
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Keyword(s):
1992 ◽
Vol 65
(1)
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pp. 111-120
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2014 ◽
Vol 5
(1)
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pp. 17-22
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2000 ◽
Vol 50
(3)
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pp. 353-356
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2008 ◽
Vol 56
(10)
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pp. 1417-1422
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2003 ◽
Vol 33
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pp. 219-230
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