Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog.

The acid-catalyzed isomerization of the diglyceride analog (1,2,3/0)-1,2-dipalmitoylcyclopentane-1,2,3-triol has been used to generate syn-syn-1,3-diacyl-cyclopentane-1,2,3-triol, a required intermediate in the synthesis of a symmetrical all-cis-1,2,3/0-2P cyclopentanoid phosphatidic acid analog. Th...

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Bibliographic Details
Main Authors: A J Hancock, M D Lister
Format: Article
Language:English
Published: Elsevier 1979-02-01
Series:Journal of Lipid Research
Online Access:http://www.sciencedirect.com/science/article/pii/S0022227520406406
Description
Summary:The acid-catalyzed isomerization of the diglyceride analog (1,2,3/0)-1,2-dipalmitoylcyclopentane-1,2,3-triol has been used to generate syn-syn-1,3-diacyl-cyclopentane-1,2,3-triol, a required intermediate in the synthesis of a symmetrical all-cis-1,2,3/0-2P cyclopentanoid phosphatidic acid analog. The all-cis cyclo-phosphatidic acid analog has therefore been obtained in the free acid form and as the diphenyl ester, dimethyl ester, and dipotassium salt derivatives. The compounds have been characterized by microanalysis and spectroscopic methods. The 1,2,3/0-2P analog is now available for comparative studies with the corresponding all-trans cyclophosphatidic acid (1,3/2-2P).
ISSN:0022-2275