Artículo
Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L
Arroyo Aguilar, Abel Alfredo
; Ledesma, Gabriela Nanci
; Tirloni, Bárbara; Kaufman, Teodoro Saul
; Larghi, Enrique Leandro
Fecha de publicación:
08/2019
Editorial:
Georg Thieme Verlag Kg
Revista:
Synthesis-stuttgart
ISSN:
0039-7881
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The first total synthesis of melovinone, a nonrutaceous 3-methoxy-4-quinolone alkaloid isolated from Melochia tomentosa L., is reported. The target was acquired in a convergent fashion through the Suzuki?Miyaura cross-coupling reaction between an ortho-nitrobenzoic acid acetonyl ester derivative prepared from vanillin and potassium 5-phenyl-1-pentyltrifluoroborate, obtained from β-phenethyl bromide. The coupling was followed by a chemoselective reduction of the nitro group and a microwave-assisted and AcOH-promoted cyclization with rearrangement of the resulting acetonyl anthranilate. This afforded a pseudane intermediate, which was selectively methylated on the 3-OH. The synthetic pathway enabled to reach the objective in 11 steps and 18% overall yield. The 1H NMR spectra of the synthetic and natural product were in full agreement.
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Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Articulos de INST.DE QUIMICA ROSARIO
Citación
Arroyo Aguilar, Abel Alfredo; Ledesma, Gabriela Nanci; Tirloni, Bárbara; Kaufman, Teodoro Saul; Larghi, Enrique Leandro; Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L; Georg Thieme Verlag Kg; Synthesis-stuttgart; 51; 22; 8-2019; 4253-4262
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