Artículos de revistas
Expedient Approach to 6-Bromo-2-isopropylidenecoumaranone, a Potential Intermediate for the Synthesis of TMC-120B, Pseudodeflectusin, and Their Congeners
Fecha
2016-05Registro en:
Pergomet, Jorgelina Leonor; Kaufman, Teodoro Saul; Bracca, Andrea Beatriz Juana; Expedient Approach to 6-Bromo-2-isopropylidenecoumaranone, a Potential Intermediate for the Synthesis of TMC-120B, Pseudodeflectusin, and Their Congeners; Wiley VCH Verlag; Helvetica Chimica Acta; 99; 5; 5-2016; 398-404
0018-019X
CONICET Digital
CONICET
Autor
Pergomet, Jorgelina Leonor
Kaufman, Teodoro Saul
Bracca, Andrea Beatriz Juana
Resumen
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.