β-Oxy-α-diazo carbonyl compounds. III. Rh2(AcO)4 mediated decomposition of β-acetoxy-α-diazo esters. Application to the synthesis of natural 3-deoxy-2-keto aldonic acids (KDO and DAH)
1994; Elsevier BV; Volume: 35; Issue: 36 Linguagem: Inglês
10.1016/s0040-4039(00)73473-3
ISSN1873-3581
AutoresF. J. LOPEZ‐HERRERA, Francisco Sarabia-García,
Tópico(s)Enzyme Catalysis and Immobilization
Resumoβ-Acetoxy-α-diazo esters yield α-enol acetate esters quantitatively by reaction with dirhodium tetraacetate. The reaction was used to prepare the major natural compounds 3-Deoxy-D-arabino-2-Heptulosonic acid (DAH, 1) and 3-Deoxy-D-manno-2-Octulosonic acid (KDO, 2) by conversion of the enol acetate function to the corresponding ketone.
Referência(s)