Journal
SYNTHESIS-STUTTGART
Volume 51, Issue 22, Pages 4253-4262Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690164
Keywords
melovinone; total synthesis; natural products; nonrutaceous alkaloids; 3-methoxy-4-quinolones
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Funding
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET) [PUE-0006-2016]
- Agencia Nacional de Promocion Cientifica y Tecnologica (ANPCyT) [PICT 2014-0445, PICT 2017-0149]
- CONICET
- Agencia Santafesina de Ciencia, Tecnologia e Innovacion Productiva (ASACTeI) [AC 2015-0005]
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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 beta-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 (1) H NMR spectra of the synthetic and natural product were in full agreement.
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