Synthesis, crystal structure and absolute configuration of (3a<i>S</i>,4<i>R</i>,5<i>S</i>,7a<i>R</i>)-7-(but-3-en-1-yn-1-yl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-2<i>H</i>-1,3-benzodioxole-4,5-diol
The absolute configuration of the title compound, C<sub>13</sub>H<sub>16</sub>O<sub>4</sub>, determined as 1<i>S</i>,2<i>R</i>,3<i>S</i>,4<i>R</i> based on the synthetic pathway, was confirmed by single-crystal X-ray diffraction. The mol-ecule is a relevant inter-mediary for the synthesis of speciosins, ep-oxy-quinoides or their analogues. The mol-ecule contains fused five- and six-membered rings with two free hydroxyl groups and two protected as an iso-propyl-idenedioxo ring. The packing is directed by hydrogen bonds that define double planes of mol-ecules laying along the <i>ab</i> plane and van der Waals inter-actions between aliphatic chains that point outwards of the planes.
Authors
- Leopoldo Suescun (ORCID: https://orcid.org/0000-0002-7606-8074)
- Alejandro Peixoto de Abreu Lima
- Valeria Schapiro (ORCID: https://orcid.org/0000-0002-5794-0760)
- Enrique Pandolfi
Institutions
- Universidad de la República de Uruguay (UY)
- Instituto de Química Orgánica General (ES)
- Centro Uruguayo de Imagenología Molecular (UY)
Publication Details
- Journal
- Acta Crystallographica Section E Crystallographic Communications
- Published
- 2024-10-11
- DOI
- https://doi.org/10.1107/s2056989024009733
- Primary Topic
- Plant Toxicity and Pharmacological Properties
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Agencia Nacional de Investigación e Innovación
- Universidad de la República Uruguay