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Synthesis of methyl [5,6,8,9,14,‐ 3 H 6 ]‐hepoxilin B 3 and its conversion into methyl [5,6,8,9,14,15‐ 3 H 6 ]‐hepoxilin A 3
Author(s) -
Demin P. M.,
Pivnitsky K. K.,
Vasiljeva L. L.,
PaceAsciak C. R.
Publication year - 1994
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580340304
Subject(s) - allylic rearrangement , chemistry , benzoates , mitsunobu reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis
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.