Synthesis of d-arabinose-derived polyhydroxylated pyrrolidine, indolizidine and pyrrolizidine alkaloids. Total synthesis of hyacinthacine A2 |
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| Authors: | Ignacio Delso Andrea Goti |
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| Institution: | a Laboratorio de Sintesis Asimetrica, Departamento de Quimica Organica, Instituto de Ciencia de Materiales de Aragon, Universidad de Zaragoza, CSIC, 50009 Zaragoza. Aragon, Spain
b Dipartimento di Chimica Organica Ugo Schiff and HeteroBioLab, Università di Firenze, associated with ICCOM-CNR, via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy |
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| Abstract: | Several new polyhydroxylated alkaloids including pyrrolidines with a long side chain and 3-(hydroxymethyl) indolizidines were prepared from a common nitrone easily obtained from d-arabinose. In addition, a total synthesis of hyacinthacine A2 has been achieved in five steps and 67.7% overall yield starting from the same d-arabino-derived nitrone. All synthesized compounds have a common structural feature consisting of a pyrrolidine ring with d-arabino configuration. |
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| Keywords: | Alkaloids Pyrrolidines Nitrones |
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