Synthesis of polyhydroxycyclohexanes and relatives from (-)-quinic acid.
An efficient and versatile strategy for the synthesis of polyhydroxycyclohexanes and related compounds 3-6 is reported. The successful synthesis of these analogues has been achieved from a common intermediate, quinic acid derived lactone 2, rapidly accessible from cheap and commercially available (-)-quinic acid (1) as a chiral template. A practical route involving stereocontrolled epoxide formation and hydrolysis has been developed for the synthesis of 2,3-trans analogues 3 and 4. The preparation of the 2,3-cis analogues 5 and 6 has been realized by diasteroselective oxidation of a 5,6-double bond.
González
Concepción
C
Departamento de Química Orgánica y Unidad Asociada al C.S.I.C., Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain. cgb1@lugo.usc.es
Carballido
Montserrat
M
Castedo
Luis
L
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D003510:Cyclohexanes / Q000138:chemical synthesis*; D006900:Hydroxylation; D007202:Indicators and Reagents; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis*; D011801:Quinic Acid / Q000737:chemistry*; D013237:Stereoisomerism
D003510:Cyclohexanes; D007202:Indicators and Reagents; D007783:Lactones; D011108:Polymers; D011801:Quinic Acid