125304-87-2Relevant academic research and scientific papers
Palladium-catalyzed oxime ether directed regioselective C-H alkoxylation of arenes
Pan, Liang,Wang, Liang,Chen, Qun,He, Mingyang
, p. 1981 - 1988 (2016)
A palladium-catalyzed highly regioselective ortho-C(sp2)-H alkoxylation of oxime ethers with PhI(OAc)2as the oxidant and alcohols as the alkoxylation reagents has been developed. Mono-alkoxylated and acetoxylated products could be selectively obtained via tuning the reaction conditions. A series of oxime ethers were tolerated, affording the corresponding products in moderate to good yields. Both primary and secondary alcohols survived the reaction conditions. Moreover, the directing group can be easily removed, thereby providing a straightforward access to substituted aryl ketones.
Rhodium(III)-Catalyzed C-H Activation-Based First Total Synthesis of 6- O -Methyl Anciscochine, an Alkaloid Isolated from Ancistrocladus tectorius
Kaufman, Teodoro S.,Larghi, Enrique L.,Romero, Brenda S.,Vargas, Didier F.
, p. 119 - 126 (2020)
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 43percent, involved the oximation of commercial 2,4-dimethoxyacetophenone under CeCl 3 ·7H 2 O-promotion, followed by pivaloylation of the oxime. A one-pot pivaloxime-directed alkenyl-ation/annulation stage with methyl acrylate, furthered by a NaBH 4 / CaCl 2- -mediated reduction of the resulting isoquinoline 3-carboxylate ester completed the sequence.
A Ruthenium-Catalyzed C-H Activation Strategy as an Efficient Shortcut in the Total Synthesis of 6,8-Dimethoxy-1,3-dimethyl?-isoquinoline
Fonzo, Santiago,Kaufman, Teodoro S.,Vargas, Didier F.
, p. 3908 - 3914 (2019)
A short and convenient total synthesis of 6,8-dimethoxy-1,3-dimethylisoquinoline, employing a C-H activation/alkenylation strategy, is reported. The approach involves the CeCl 3 7H 2 O-promoted methoximation of 2,4-dimethoxyacetophenone and a methoxime-directed ruthenium-catalyzed allylation. This was followed by a one-pot, ruthenium-catalyzed allyl to propenyl isomerization and a microwave-assisted 6π-azaelectrocylization to complete the sequence. This approach, which entails a shortcut in the synthetic management of the three-carbon side chain, is an improved and more efficient route toward the natural product, which facilitated its access in just three steps and 27.3percent overall yield.
