Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
The total synthesis and structural revision of (+)-cryptoconcatone H are described. Guided by computational studies for the final structure assignment, the stereogenic centers at the tetrahydropyran moiety of (+)-cryptoconcatone H were assembled through catalytic asymmetric methodologies: Krische al...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2017 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/53198 |
| Acceso en línea: | http://hdl.handle.net/11336/53198 |
| Access Level: | acceso abierto |
| Palabra clave: | CATALYTIC ASYMMETRIC SYNTHESIS STEREOCHEMICAL REVISION CRYPTOCONCATONE H DP4+ CALCULATIONS https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | The total synthesis and structural revision of (+)-cryptoconcatone H are described. Guided by computational studies for the final structure assignment, the stereogenic centers at the tetrahydropyran moiety of (+)-cryptoconcatone H were assembled through catalytic asymmetric methodologies: Krische allylation, cross-metathesis reaction, and THP formation via Pd(II)-catalyzed cyclization. Finally, a Krische allylation reaction established the last stereocenter, and the lactone moiety was formed by ring-closing metathesis. |
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