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Hypocholesterolemic alkaloids of lentinus edodes (berk.) sing. II. A novel synthesis of eritadenine
Author(s) -
Kamiya T.,
Saito Y.,
Hashimoto M.,
Seki H.
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090230
Subject(s) - chemistry , lentinus , uracil , thymine , yield (engineering) , cytosine , condensation , oxide , stereochemistry , organic chemistry , medicinal chemistry , mushroom , biochemistry , dna , food science , materials science , physics , metallurgy , thermodynamics
A novel and convenient method for the synthesis of eritadenine (I) was established. Direct condensation of adenine and 2,3‐ O ‐isopropylidene‐ D ‐erythronolactone (II) under basic condition, followed by removal of the protecting group, afforded eritadenine (I) in fairly good yield, with accompany of a small amount of the N 3 ‐isomer (VI). A similar reaction of adenine 1‐oxide gave exclusively eritadenine oxide (VII), which was catalytically reduced to give eritadenine (I). This procedure also provided pyrimidinyl derivatives (VIII, IX and X) corresponding to cytosine, uracil, and thymine.