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Synthesis 2020; 52(01): 119-126
DOI: 10.1055/s-0039-1690701
DOI: 10.1055/s-0039-1690701
paper
Rhodium(III)-Catalyzed C–H Activation-Based First Total Synthesis of 6-O-Methyl Anciscochine, an Alkaloid Isolated from Ancistrocladus tectorius
Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET, PUE IQUIR-2016) and Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT, PICT 2017-0149). D.F.V. thanks CONICET for his Doctoral fellowship.Weitere Informationen
Publikationsverlauf
Received: 28. August 2019
Accepted after revision: 17. September 2019
Publikationsdatum:
10. Oktober 2019 (online)
Abstract
The concise and efficient first total synthesis of 6-O-methyl anciscochine, employing a tandem C–C/C–N formation approach via a rhodium-catalyzed C–H activation/alkenylation/annulation strategy, is reported. This heterocycle was isolated from the liana Ancystrocladus tectorius and features a unique 3-hydroxymethylisoquinoline core that is found in a few other natural products and in some bioactive synthetic compounds. The synthesis, which was executed in four high-yielding steps and a global yield of 43%, involved the oximation of commercial 2,4-dimethoxyacetophenone under CeCl3·7H2O-promotion, followed by pivaloylation of the oxime. A one-pot pivaloxime-directed alkenylation/annulation stage with methyl acrylate, furthered by a NaBH4/ CaCl2-mediated reduction of the resulting isoquinoline 3-carboxylate ester completed the sequence.
Key words
C–H activation - natural product - rhodium catalysis - 6-O-methyl anciscochine - Ancystrocladus tectorius - one-pot alkenylation/ annulationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690701.
- Supporting Information
-
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