137469-85-3Relevant academic research and scientific papers
Late-stage and strain-accelerated oxidation enabled synthesis of haouamine A
Chen, David Y.-K.,Park, Kun Ho,Rizzo, Antonio
, p. 8132 - 8137 (2020)
Herein we report a new synthetic entry to the strained cyclophane alkaloid natural product, haouamine A. The successful strategy featured a rhodium-catalyzed diazo-insertion reaction to install the all-carbon quaternary center and a rhodium-catalyzed intramolecular aziridination reaction to establish the nitrogen-bearing stereocenter, of the target molecule. Most notably, a late-stage, site-selective and strain-accelerated oxidation of a deoxygenated macrocyclic intermediate was successfully implemented, and in doing so provided a novel solution to the infamous biphenol cyclophane system of haouamine A.
An efficient, one-pot transamidation of 8-aminoquinoline amides activated by tertiary-butyloxycarbonyl
Wu, Wengang,Yi, Jun,Xu, Huipeng,Li, Shuangjun,Yuan, Rongxin
, (2019/04/05)
The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C(acyl)–N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields.
Palladium-catalyzed direct C-H silylation and germanylation of benzamides and carboxamides
Kanyiva, Kyalo Stephen,Kuninobu, Yoichiro,Kanai, Motomu
supporting information, p. 1968 - 1971 (2014/05/06)
A palladium-catalyzed regioselective activation of C(sp2)-H and C(sp3)-H bonds of benzamides and carboxamides, followed by coupling with disilanes to afford organosilanes in moderate to high yields, with the aid of 8-aminoquinoline as a directing group, is reported. Catalytic C(sp 2)-H germanylation of benzamides also proceeds under the same palladium catalysis. The reaction tolerates a wide variety of functional groups and is scalable without yield reduction. The bidentate directing group is readily removed and recovered by the reaction with a hydrazine, with concominant generation of an acyl hydrazide.
Synthesis of the LeuTrp component of the celogentin family of cyclic peptides through a CH activationcross-coupling strategy
Li, Barbara T. Y.,White, Jonathan M.,Hutton, Craig A.
experimental part, p. 438 - 444 (2010/08/06)
A bioinspired approach to the central leucine(C3)-tryptophan(C6) cross-linked moiety present in the celogentin family of cyclic peptide natural products was achieved. The key transformation was enabled through a palladium-catalyzed C-H activationcross-coupling of leucine quinoline amide and 6-iodotryptophan derivatives. X-Ray crystallographic analysis of a β-(indol-6-yl)-leucine derivative confirms the stereochemistry of the cross-linked adduct matches that of the natural products. The method enables the preparation of the Leu-Trp adduct as a single stereoisomer from l-leucine and l-tryptophan.
Total synthesis of celogentin C by stereoselective C-H activation
Feng, Yiqing,Chen, Gong
supporting information; experimental part, p. 958 - 961 (2010/06/11)
(Figure Presented) A total gent: Inspired by the biosynthesis of celogentin C, a highly stereoselective and efficient palladium-catalyzed C-H functionalization strategy is employed to construct the key Leu-Trp linkage of this bicyclic compound. A streamlined synthesis is completed in 23 steps from simple amino acid building blocks.
