Preparation of carbocyclic S-adenosylazamethionine accompanied by a practical synthesis of (-)-aristeromycin.
For the preparation of a carbocyclic nitrogen analogue of S-adenosylmethionine (carba-AdoazaMet, 4), a practical synthesis of (-)-aristeromycin (7) has been developed using variations of literature procedures. This approach called for a stereospecific synthesis of (3aR,6aR)-2,2-dimethyl-3a,6a-dihydrocyclopenta[1,3]dioxol-4-one ((4R, 5R)-4,5-O-isopropylidene-2-cyclopentenone) (8), which was achieved by modifying reported procedures from D-(-)-ribose.
Yang
Minmin
M
Department of Chemistry, Auburn University, Auburn, Alabama 36849-5312, USA.
Ye
Wei
W
Schneller
Stewart W
SW
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis*; D008968:Molecular Conformation; D012436:S-Adenosylmethionine / Q000138:chemical synthesis*
D001372:Aza Compounds; C030034:aristeromycin; D012436:S-Adenosylmethionine; D000241:Adenosine