Organic Chemistry Portal
Organic Chemistry Highlights

Monday, October 10, 2022
Douglass F. Taber
University of Delaware

Substituted Benzenes: The Zhai Synthesis of Cephanolide B

Shangda Li and Gang Li of the Fujian Institute of Research on the Structure of Matter used the iodo nitro aromatic 2 to selectively iodinate the anilide 1, leading to 3 (Org. Lett. 2022, 24, 3657. DOI: 10.1021/acs.orglett.2c01283). Hui Gao, Zhi Zhou and Wei Yi of the Guangzhou Medical University rearranged the phenoxysulfonamide 4 to the o-sulfonamidophenol 5 (Tetrahedron Lett. 2022, 89, 153601. DOI: 10.1016/j.tetlet.2021.153601).

Hang Shi of Westlake University coupled the phenol 6 with piperidine 7 to give the aryl amine 8 (J. Am. Chem. Soc. 2022, 144, 1144. DOI: 10.1021/jacs.1c12622). Lin Yu and Wengui Duan of Guangxi University coupled pyrrole 10 with the nitro aromatic 9, leading to the protected aniline 11 (Org. Chem. Front. 2022, 9, 2351. DOI: 10.1039/D2QO00010E).

Veera Reddy Yatham of the Indian Institute of Science Education and Research devised conditions for coupling the bromobenzene 12 with the secondary iodide 13, to give 14 (J. Org. Chem. 2022, 87, 5442. DOI: 10.1021/acs.joc.2c00251). Chuanhu Lei of Shanghai University and Jian Jin of the Shanghai Institute of Organic Chemistry prepared the styrene derivative 17 by coupling vinyl acetate 16 with the bromobenzene 15 (Org. Lett. 2022, 24, 354. DOI: 10.1021/acs.orglett.1c04018).

Shun-Jun Ji and Yingsheng Zhao of Soochow University established conditions for adding a carboxyl group para on anisole 18, to give 19 (Org. Lett. 2022, 24, 2155. DOI: 10.1021/acs.orglett.2c00417). Debabrata Maiti of the Indian Institute of Technology Bombay effected the direct oxidative Heck coupling of anisole 18 with methyl acrylate 20, leading to the ester 21 (J. Am. Chem. Soc. 2022, 144, 1929. DOI: 10.1021/jacs.1c12311). Giovanni Poli of Sorbonne Université and Gianluigi Broggini of the Università degli Studi dell’Insubria assembled the sulfonamide 24 by coupling 4-methyl anisole 22 with the O-allyl carbamate 23 (Org. Chem. Front. 2022, 9, 1711. DOI: 10.1039/D2QO00114D). Dattatraya H. Dethe of the Indian Institute of Technology Kanpur achieved significant enantiomeric excess in the preparation of the lactone 26 by the coupling of the benzoic acid 25 with methyl acrylate 20 (J. Org. Chem. 2022, 87, 4617. DOI: 10.1021/acs.joc.1c02961).

Haifeng Yu and Wenju Wang of Baicheng Normal University assembled the benzamide 29 by adding nitroethane 28 to the ketene dithioacetal 27 (J. Org. Chem. 2022, 87, 2985. DOI: 10.1021/acs.joc.1c02825). Ravindar Kontham of CSIR-National Chemical Laboratory showed that the intial adduct between the enone 30 and the alkyne 31 aromatized, leading to the chromane 32 (Org. Chem. Front. 2022, 9, 802. DOI: 10.1039/D1QO01643A).

The cephanolide diterpenoids isolated from the coniferous shrub Cephalotaxus sinensis, exemplified by cephanolide B (37), show antineoplastic, antiviral and antitumor properties. Hongbin Zhai of the Shenzhen Graduate School of Peking University established a route to cephanolides A-D, based on the construction of the tetracyclic ketone 36 by the cyclization of the alkyne 34 with the alkyne 35 (J. Am. Chem. Soc. 2022, 144, 10640. DOI: 10.1021/jacs.2c03978).

D. F. Taber, Org. Chem. Highlights 2022, October 10.