Two key chiral intermediates in a new 4-hydroxyisoleucine synthesis.
We present the crystal and molecular structure of two key compounds of a new synthesis strategy for isomers of natural (2S,3R, 4S)-4-hydroxyisoleucines, 2,3,5,6,7, 8-hexahydro-3-(1-hydroxy-1-methyl-2-oxopropyl)-6,8-methano-7,7, 8a-trimethyl-5H-1,4-benzoxazin-2-one, C(16)H(23)NO(4), and 2,3,5,6,7, 8-hexahydro-3-(1-methyl-2-oxopropyl)-6,8-methano-7,7, 8a-trimethyl-5H-1,4-benzoxazin-2-one, C(16)H(23)NO(3). A new optically pure chiral oxazinone auxiliary derived from (1R,2R, 5R)-2-hydroxypinan-3-one was used.
Kassem
T
T
Laboratoire des Aminoacides, Peptides et Protéines, Université Montpellier I et II, Faculté de Pharmacie, UMR CNRS 5810, 15 Avenue Charles Flahault, 34060 Montpellier CEDEX 2, France.
Rolland
V
V
Martinez
J
J
Rolland
M
M
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007532:Isoleucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
C104672:4-hydroxyisoleucine; D007532:Isoleucine