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J Org Chem. 2003 Aug 22;68(17):6760-6.

Direct synthesis of plasmenylcholine from allyl-substituted glycerols.

Author information

1
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.

Abstract

We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxy-protected 1-allylglycerol precursors with s-BuLi at -65 to -80 degrees C. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.

PMID:
12919045
DOI:
10.1021/jo026826w
[Indexed for MEDLINE]

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