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

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

The selective tritiation of methyl 10(R/S)‐hydroxy‐11(R),12(S)‐epoxyeicosa‐5,8,14‐triynoate into two C10‐epimeric [3H6]‐hepoxilins B3 methyl esters is described. These compounds are subsequently converted into two C8‐epimeric [3H6]‐hepoxilins A3 methyl esters by allylic rearrangement under Mitsunobu...

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Veröffentlicht in:Journal of labelled compounds & radiopharmaceuticals 1994-03, Vol.34 (3), p.221-230
Hauptverfasser: Demin, P. M., Pivnitsky, K. K., Vasiljeva, L. L., Pace-Asciak, C. R.
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
allylic rearrangement
Chemistry
Exact sciences and technology
hepoxilin A3
hepoxilin B3
Mitsunobu inversion
Organic chemistry
Preparations and properties
tritiation
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Zusammenfassung:The selective tritiation of methyl 10(R/S)‐hydroxy‐11(R),12(S)‐epoxyeicosa‐5,8,14‐triynoate into two C10‐epimeric [3H6]‐hepoxilins B3 methyl esters is described. These compounds are subsequently converted into two C8‐epimeric [3H6]‐hepoxilins A3 methyl esters by allylic rearrangement under Mitsunobu conditions via corresponding benzoates.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.2580340304