[PMID]: | 25110185 |
[Au] Autor: | Mondal S; Sureshan KM |
[Ad] Endereço: | School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram 695016, India. kms@iisertvm.ac.in. |
[Ti] Título: | Total syntheses and structural validation of lincitol A, lincitol B, uvacalol I, uvacalol J, and uvacalol K. |
[So] Source: | Org Biomol Chem;12(37):7279-89, 2014 Oct 07. |
[Is] ISSN: | 1477-0539 |
[Cp] País de publicação: | England |
[La] Idioma: | eng |
[Ab] Resumo: | Natural carbasugars are an important class of biologically active compounds. Due to their conformational freedom and the subtle difference in spectral characteristics between isomers, often their NMR-based structural assignments are erroneous. It is thus important to validate their structural identity through chemical synthesis. We report the first total syntheses and structural validation of five natural carbasugars, namely, lincitol A, lincitol B, uvacalol I, uvacalol J, and uvacalol K in their racemic forms, from a myo-inositol-derived common intermediate. This intermediate was synthesized by the vinylogous ring opening of myo-inositol orthoester cage under mild acidic conditions in six steps from myo-inositol. From this intermediate, we achieved the syntheses of (±)-lincitol A in six steps, (±)-lincitol B in seven steps, (±)-uvacalol I in five steps, (±)-uvacalol J in five steps, and (±)-uvacalol K in seven steps. The structure and relative stereochemistry of these natural products were confirmed by comparing the (1)H and (13)C NMR spectra of synthesised natural products with the reported data. These syntheses involved several unprecedented protecting-group manipulations and unexpected reactivities. |
[Mh] Termos MeSH primário: |
Produtos Biológicos/química Produtos Biológicos/síntese química Carbaçúcares/síntese química
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[Mh] Termos MeSH secundário: |
Carbaçúcares/química Conformação Molecular Estrutura Molecular Estereoisomerismo
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[Pt] Tipo de publicação: | JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T |
[Nm] Nome de substância:
| 0 (Biological Products); 0 (Carbasugars) |
[Em] Mês de entrada: | 1507 |
[Cu] Atualização por classe: | 140828 |
[Lr] Data última revisão:
| 140828 |
[Sb] Subgrupo de revista: | IM |
[Da] Data de entrada para processamento: | 140812 |
[St] Status: | MEDLINE |
[do] DOI: | 10.1039/c4ob01329h |
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