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Über Pterinchemie 76. Mitteilung [1] Eine einfache Synthese von Leucovorin
Author(s) -
Khalifa Esam,
Ganguly Abhoy N.,
Bieri Jost H.,
Viscontini Max
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630850
Subject(s) - chemistry , formylation , diastereomer , folic acid , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine
A Convenient Synthesis of Leucovorin The synthesis of leucovorin, a 5‐formyl‐(6 R or S )‐5,6,7,8‐tetrahydropteroyl‐ L ‐glutamic acid (II) is described. The L ‐folic acid was first reduced to (6 R , S )‐tetrahy‐dro‐ L ‐folic acid (I); formylation with methyl‐formate in DMSO gave directly leucovorin (as a diastereomeric mixture) in good yields. To demonstrate, that the formylation occurred regiospecifically at N (5) and not at N (10), N (10)‐nitroso‐(6 R , S )‐tetrahydro‐ L ‐folic acid was formylated under the same conditions. Reductive elimination of the N (10)‐nitrosogroup gave the identical leucovorin as in the previous case. The synthetic leucovorin was biologically as active as the natural product with Streptococcus faecalis ATCC 8043 and Pediococcus cerevisiae ATCC 8081.