Elsevier

Tetrahedron Letters

Volume 43, Issue 15, 8 April 2002, Pages 2801-2805
Tetrahedron Letters

The first total synthesis of iPF-VI and its deuterated analog

https://doi.org/10.1016/S0040-4039(02)00398-2Get rights and content

Abstract

The total and stereospecific syntheses of iPF-VI and d4-iPF-VI have been accomplished. iPF-VI is a docosahexanenoic acid (DHA)-derived isoprostane. DHA is the most abundant polyunsaturated fatty acid in the brain. Different synthetic designs have been used for the two syntheses. In the d4-iPF-VI design, the deuterated part of the molecule was introduced last in the synthesis.

Stereospecific syntheses of DHA-derived isoprostane iPF-VI and its d4 analog are reported.

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Acknowledgements

We wish to acknowledge the NIH for support under Grants DK-44730 (J.R.), HL-54500, and HL-62250 (G.A.F.); the AHA for support under Grant 0030211 (D.P.); and the NSF for an AMX-360 NMR instrument (Grant CHE-90-13145).

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