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Synthesis of methyl [5,6,8,9,14,-3 H6]-hepoxilin B3 and its conversion into methyl [5,6,8,9,14,15-3H6]-hepoxilin A3

✍ Scribed by P. M. Demin; K. K. Pivnitsky; L. L. Vasiljeva; C. R. Pace-Asciak

Publisher: John Wiley and Sons
Year: 1994
Tongue: French
Weight: 462 KB
Volume: 34
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580340304

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✦ Synopsis

Abstract

The selective tritiation of methyl 10(R/S)‐hydroxy‐11(R),12(S)‐epoxyeicosa‐5,8,14‐triynoate into two C^10^‐epimeric [^3^H~6~]‐hepoxilins B~3~ methyl esters is described. These compounds are subsequently converted into two C^8^‐epimeric [^3^H~6~]‐hepoxilins A~3~ methyl esters by allylic rearrangement under Mitsunobu conditions via corresponding benzoates.

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