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 Autoren Institutsangaben 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 Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) 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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