Organic Chemistry Portal
Organic Chemistry Highlights

Monday, October 9, 2023
Douglass F. Taber
University of Delaware

Substituted Benzenes: The Newhouse Synthesis of Shearilicine

Haibo Ge of Texas Tech University and Debabrata Maity of the Indian Institute of Technology Bombay effected the m-acetoxylation of the ester 1, leading to 2 (JACS Au 2023, 3, 1790. DOI: 10.1021/jacsau.3c00231). Dauquan Tu of Jiangsu Hansoh Pharmaceutical Co. and Jun Luo and Chao Jiang of the Nanjing University of Science and Technology cyclized the amide 3 to the lactam 4 (Org. Chem. Front. 2023, 10, 109. DOI: 10.1039/D2QO01562E).

Michael J. James of the University of Manchester used the oxime 6 to convert the nitroaromatic 5 to the phenol 7 (Chem. Eur. J. 2023, 29, e202203807. DOI: 10.1002/chem.202203807). Gašper Tavčar of the Jožef Stefan Institute prepared the fluoroaromatic 10 by the deoxyfluorination of the phenol 8 with the imidazolium 9 (Org. Lett. 2023, 25, 3649. DOI: 10.1021/acs.orglett.3c01018).

Daniel J. Weix of the University of Wisconsin coupled the benzoate 11 with the pyridinium salt 12, leading to the alkylated benzene derivative 13 (J. Am. Chem. Soc. 2023, 145, 9951. DOI: 10.1021/jacs.2c11552). David J. Procter, also of the University of Manchester, used blue light to promote the assembly of the ketone 17 by the coupling of the silyl enol ether 16 with the triaryl sulfonium salt derived from the combination of 14 and 15 (Nature Chem. 2023, 15, 43. DOI: 10.1038/s41557-022-01092-y).

Sébastien Prévost of the Ecole Polytechnique employed a transient directing group strategy to prepare the ester 20, coupling the aldehyde 18 with the oxalate salt 19 (Org. Lett. 2023, 25, 1380. DOI: 10.1021/acs.orglett.3c00086). Ruzhang Liu of Yangzhou University prepared the tetrahydrofuran 23 by combining the unsaturated alcohol 22 with the triarylsulfonium salt derived from 21 (Org. Lett. 2023, 25, 2606. DOI: 10.1021/acs.orglett.3c00582). Xuegong She of Lanzhou University cyclized the amide 24 to the lactam 25 (Org. Lett. 2023, 25, 1003. DOI: 10.1021/acs.orglett.3c00132). Takehiko Yoshimitsu of Okayama University used sunlight to promote the coupling of the N-hydroxyphthalimide ester 26 with ethyl acrylate 27, leading to the ester 28 (J. Org. Chem. 2023, 88, 1085. DOI: 10.1021/acs.joc.2c02552).

Daniele Leonori of RWTH Aachen University oxidized the β-ketoester 29 to the methyl salicylate 30 (Angew. Chem. Int. Ed. 2023, 62, e202301656. DOI: 10.1002/anie.202301656). Christopher J. T. Hyland and Stephen G. Pyne of the University of Wollongong and Scott G. Stewart of the University of Western Australia cyclized the enediyne 31 to the dihydroisoindole 32 (J. Org. Chem. 2023, 88, 5391. DOI: 10.1021/acs.joc.2c03040).

The carbazole alkaloid shearilicine (35), isolated from an endophytic Penicillium species, showed interesting selective cytotoxicity. Timothy R. Newhouse of Yale University constructed 34, with the central benzene ring of 35, by cyclizing the bromoindole 33 (J. Am. Chem. Soc. 2023, 145, 4394. DOI: 10.1021/jacs.2c13584).

D. F. Taber, Org. Chem. Highlights 2023, October 9.