Diastereoselective amidoalkylation of (3S,7aR)-6-benzyl-7-hydroxy-3-phenyltetra- hydro-5H-imidazo[1,5-c][1,3]thiazol-5-one: a short and highly efficient synthesis of (+)-biotin.
A short and highly efficient synthesis of (+)-biotin in 10 steps with 20% overall yield has been achieved from L-cysteine involving amidoalkylation of hydroxy imidazothiazolone 4 via an acyliminium ion intermediate to furnish C-7-substituted imidazothiazolones 5b as the key step.
Chavan
Subhash P
SP
Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune, India 411 008. spchavan@dalton.ncl.res.in
Chittiboyina
Amar G
AG
Ravindranathan
T
T
Kamat
Subhash K
SK
Kalkote
Uttam R
UR
D000478:Alkylation; D001710:Biotin / Q000138:chemical synthesis*; D007093:Imidazoles / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis*
C499765:(3S,7aR)-6-benzyl-7-hydroxy-3-phenyltetra- hydro-5H-imidazo(1,5-c)(1,3)thiazol-5-one; D007093:Imidazoles; D013844:Thiazoles; D001710:Biotin