Synthesis and stereochemistry of capreomycidine [α-(2-iminohexahydro-4-pyrimidyl)glycine]

Abstract

THE tuberculostatic peptide antibiotics of the capreomycin group, all afford, on acid hydrolysis, a new guanido-amino-acid1 which has been termed capreomycidine. On the basis of its physical and spectral properties it has been tentatively assigned structure (I) or (II).2 We report evidence which corroborates structure (I).The racemic diastereoisomers (I) and (11) were

Synthesis of cyclic guanidines

“…12 The latter method has also been extended to the preparation of the six-membered cyclic guanidine, 2-amino-3,4,5,6-tetrahydropyrimidine.12 A second approach to cyclic guanidines in wide use involves the reaction of amines with 2-methylthio-1,3-diazines (available in two steps from diamines); this procedure has been used to prepare W-alkylguanidines of a wide variety. [13][14][15][16] Two other routes into the cyclic guanidine system, which have limited applicability, are hydrogenation of a 2-aminopyrimidine to obtain a 2-amino-3,4,5,6-tetra-hydropyrimidine16 and the fusion of guanidine with 4,5diamino-6-hydroxypyrimidine to afford 8-amino-6-* To whom correspondence should be addressed. hydroxypurine.17 We now report a synthesis via S,Sdimethyl-W-tosyliminodithiocarbonimidate as an alternative to the above.…”