Synthesis, Inhaltsverzeichnis Synthesis 2020; 52(01): 119-126DOI: 10.1055/s-0039-1690701 paper © Georg Thieme Verlag Stuttgart · New YorkRhodium(III)-Catalyzed C–H Activation-Based First Total Synthesis of 6-O-Methyl Anciscochine, an Alkaloid Isolated from Ancistrocladus tectorius Didier F. Vargas ∗ a Instituto de Química Rosario (IQUIR, CONICET-UNR), 2000 Santa Fe, Argentina eMail: vargas@iquir-conicet.gov.ar eMail: kaufman@iquir-conicet.gov.ar b Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000) Rosario, Argentina , Brenda S. Romero b Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000) Rosario, Argentina , Enrique L. Larghi a Instituto de Química Rosario (IQUIR, CONICET-UNR), 2000 Santa Fe, Argentina eMail: vargas@iquir-conicet.gov.ar eMail: kaufman@iquir-conicet.gov.ar b Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000) Rosario, Argentina , Teodoro S. Kaufman ∗ a Instituto de Química Rosario (IQUIR, CONICET-UNR), 2000 Santa Fe, Argentina eMail: vargas@iquir-conicet.gov.ar eMail: kaufman@iquir-conicet.gov.ar b Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000) Rosario, Argentina› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik 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 Key wordsC–H activation - natural product - rhodium catalysis - 6-O-methyl anciscochine - Ancystrocladus tectorius - one-pot alkenylation/ annulation Volltext Referenzen References 1a Ibrahim SR. M, Mohamed GA. Fitoterapia 2015; 106: 194 1b Bringmann G, François G, Assi LA, Schlauer J. Chimia 1998; 52: 18 1c Bringmann G, Pokorny F. 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