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Synthesis 2019; 51(22): 4253-4262
DOI: 10.1055/s-0039-1690164
DOI: 10.1055/s-0039-1690164
paper
Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L.
The authors are indebted to Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) (PUE-0006-2016) and Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT) (PICT 2014-0445 and PICT 2017-0149) for financial support. AAAA acknowledges CONICET for his Doctoral fellowship. The authors also wish to thank the Agencia Santafesina de Ciencia, Tecnología e Innovación Productiva (ASACTeI) for an institutional grant (AC 2015-0005) to Instituto de Química Rosario (IQUIR) for acquisition of a 400 MHz spectrometer.
Further Information
Publication History
Received: 27 May 2019
Accepted after revision: 26 July 2019
Publication Date:
12 August 2019 (online)
Abstract
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.
Key words
melovinone - total synthesis - natural products - nonrutaceous alkaloids - 3-methoxy-4-quinolonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690164.
- Supporting Information
- CIF File
-
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