Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks
1998; Elsevier BV; Volume: 9; Issue: 11 Linguagem: Inglês
10.1016/s0957-4166(98)00178-5
ISSN1362-511X
AutoresFrancisco Sánchez-Sancho, Bernardo Herradón,
Tópico(s)Carbohydrate Chemistry and Synthesis
ResumoThe kinetic resolutions of both (±)-N-(benzyloxycarbonyl-2-(hydroxymethyl)piperidine [(±)-5] and (±)-N-(tert-butoxycarbonyl)-2-(hydroxymethyl)piperidine [(±)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)-6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2–4 steps) and proceeded with satisfactory overall yield.
Referência(s)