Organic Chemistry Portal
Organic Chemistry Highlights

Monday, March 13, 2023
Douglass F. Taber
University of Delaware

Oxidation: The Vanderwal Synthesis of 7,20-Diisocyanoadociane

Masato Matsugi of Meijo University prepared the carbamoyl azide 2 by reaction of the hydroxamic acid 1 with diphenyl phosphorazidate (Tetrahedron Lett. 2022, 95, 153727. DOI: 10.1016/j.tetlet.2022.153727). Yan Zhao of Iowa State University designed a catalyst that effected epoxidation of 1-octene 3 to 5, leaving 2-octene (4) unreacted (ACS Catal. 2022, 12, 3444. DOI: 10.1021/acscatal.2c00253).

Bor-Cherng Hong of National Chung Cheng University devised a mild protocol for converting the nitroalkane 6 to the ketone 7 (Org. Biomol. Chem. 2022, 20, 3292. DOI: 10.1039/D2OB00267A). Felix N. Castellano of North Carolina State University and Julia Rehbein and Oliver Reiser of the University of Regensburg oxidized the carboxylic acid 8 to the ketone 9 (Chem. Commun. 2022, 58, 4456. DOI: 10.1039/D2CC00570K). Xiao-Yu Liu and Yong Qin of Sichuan University prepared the ketone 11 by the oxidative cleavage of the alkene 10 (Org. Chem. Front. 2022, 9, 2135. DOI: 10.1039/D2QO00125J). Xuesong Wong of the Huazhong University of Science and Technology developed the photochemical conversion of the tertiary benzylic alcohol 12 to the ω-alkenyl ketone 13 (ACS Catal. 2022, 12, 3710. DOI: 10.1021/acscatal.2c00204).

Sukbok Chang of KAIST effected the amination of the ester 14 to give the α-amino ester 15 (Org. Lett. 2022, 24, 1088. DOI: 10.1021/acs.orglett.1c04376). Dipankar Srimani of the Indian Institute of Technology Guwahati assembled the quinazolinone 18 by the borrowed hydrogen combination of the benzamide 17 with the alcohol 16 (J. Org. Chem. 2022, 87, 5556. DOI: 10.1021/acs.joc.1c02913). Zehui Zhang of the South-Central University for Nationalities and Buxing Han of the Institute of Chemistry of the Chinese Academy of Sciences oxidized the enone 19 to the methyl ester 20 (Nature Commun. 2021, 12, 4823. DOI: 10.1038/s41467-021-25118-0). Dillip Kumar Chand of the Indian Institute of Technology Madras oxidized the cyclic ether 21 to the lactone 22 (J. Org. Chem. 2022, 87, 4061. DOI: 10.1021/acs.joc.1c02855). Guddeangadi N. Gururaja of the Central University of Gujarat converted the aldehyde 23 into the thioamide 24 (J. Org. Chem. 2022, 87, 2410. DOI: 10.1021/acs.joc.1c02307). David Milstein of the Weizmann Institute of Science observed hydrogen evolution on the coupling of the alcohol 25 with ammonia to give the amide 26 (Chem. Sci. 2022, 13, 3894. DOI: 10.1039/D1SC07102E). Zi-Qiang Rong of the Northwestern Polytechnical University reported a parallel investigation (Org. Chem. Front. 2022, 9, 1703. DOI: 10.1039/D2QO00004K).

The tetracyclic bis-isonitrile 7,20-diisocyanoadociane (29), isolated from a marine sponge, shows nanomolar antiplasmodial activity. Christopher D. Vanderwal of the University of California, Irvine prepared dehydrocryptone 28, the starting material for a synthesis of 29, by the Razdan oxidation of commercial perillaldehyde 27 (J. Org. Chem. 2022, 87, 1398. DOI: 10.1021/acs.joc.1c02700).

D. F. Taber, Org. Chem. Highlights 2023, March 13.