Novel and efficient syntheses of (-)-methyl 4-epi-shikimate and 4,5-epoxy-quinic and -shikimic acid derivatives as key precursors to prepare new analogues.
We have developed simple methods that provide a rapid entry into the synthesis of a series of quinate and shikimate analogues, including (-)-methyl 4-epi-shikimate and the 4,5-epoxy analogues of the parent acids. Epoxy derivatives of quinic and shikimic acids were converted into methyl scyllo-quinate and (+)-methyl 3-epi-shikimate, respectively, by processes involving a regio- and stereoselective epoxide ring opening. The strategies described take place through short, high-yield reaction sequences.
Sánchez-Abella
Laura
L
Departamento de Química Organica e Inorganica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006-Oviedo, Asturias, Spain.
Fernández
Susana
S
Armesto
Nuria
N
Ferrero
Miguel
M
Gotor
Vicente
V
D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; C520597:methyl 4,5-epoxy-quinic acid; C520598:methyl 4,5-epoxy-shikimic acid; C520595:methyl 4-epi-shikimate; D011801:Quinic Acid; D012765:Shikimic Acid