Aldonolactones as chiral templates in the synthesis of thiolactones, 1,3-polyols and hydroxy amino acids
The usefulness of aldonolactones as chiral templates is shown in the synthesis of varied asymmetric molecules. For example, enantiomerically pure 4-thio-D-ribono and 4-thio-L-lyxono-1,4-lactones have been respectively synthesized from D-gulono- and D-ribono-1,4-lactones. Seven carbon 1,3-polyol chai...
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| Formato: | JOUR |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00334545_v69_n3_p621_Varela |
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| Sumario: | The usefulness of aldonolactones as chiral templates is shown in the synthesis of varied asymmetric molecules. For example, enantiomerically pure 4-thio-D-ribono and 4-thio-L-lyxono-1,4-lactones have been respectively synthesized from D-gulono- and D-ribono-1,4-lactones. Seven carbon 1,3-polyol chains have been enantioselectively obtained from D-glycero-D-gulo-heptono-1,4-lactone via chiral furanone derivatives. Also, furanones and pyranones derived from D-glucosaminic acid were employed as intermediates in the synthesis of hydroxy amino acids, such as cis-4-hydroxypipecolic acid and (2S,4S,5R)-4,5,6-trihydroxynorleucine. |
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