Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners
A straightforward approach toward 6-bromo-2-isopropylidenecoumaranone, a potential intermediate toward alkaloid TMC 120-B, pseudodeflectusin, and other natural products, was reported. The synthetic sequence involved the reaction of 3-bromosalicylaldehyde with chloroacetone and cyclization of the r...
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| Autores principales: | , , |
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| Formato: | article artículo publishedVersion |
| Lenguaje: | Inglés |
| Publicado: |
Wiley
2018
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| Materias: | |
| Acceso en línea: | http://hdl.handle.net/2133/10498 http://hdl.handle.net/2133/10498 |
| Aporte de: |
| Sumario: | A straightforward approach toward 6-bromo-2-isopropylidenecoumaranone, a potential intermediate toward alkaloid TMC
120-B, pseudodeflectusin, and other natural products, was reported. The synthetic sequence involved the reaction of
3-bromosalicylaldehyde with chloroacetone and cyclization of the resulting ether to a 2-acetylcoumaranol intermediate. This
was followed by sequential methyl Grignard addition and Jones’ oxidation to the corresponding coumaranone, which was
dehydrated to the final product with the methanesulfonyl chloride/pyridine reagent. The protection of the coumaranol as the
corresponding THP-ether resulted in improved product yields. |
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