Organic Chemistry Portal
Organic Chemistry Highlights

Monday, June 15, 2020
Douglass F. Taber
University of Delaware

Heteroaromatics: The Zhang Synthesis of Suaveoline

Dingqiao Yang of South China Normal University rearranged the isoxazole 1 to the furan 2 (Adv. Synth. Catal. 2019, 361, 5634. DOI: 10.1002/adsc.201901176). Goutam Kumar Lahiri and Debabrata Maiti of the Indian Institute of Technology Bombay observed remarkable regioselectivity in the preparation of 5 by the combination of 4 with 3 (Angew. Chem. Int. Ed. 2019, 58, 11039. DOI: 10.1002/anie.201906264). Timothy J. Donohoe of the University of Oxford used photolysis to convert 6 to the pyrrole 7 (Chem. Eur. J. 2019, 25, 13114. DOI: 10.1002/chem.201903590). Aurélien Blanc of the Université de Strasbourg assembled 9 by rearranging 8 to an intermediate tosylate, that was then coupled with phenylboronic acid (Org. Lett. 2019, 21, 5542. DOI: 10.1021/acs.orglett.9b01860).

Heesoon Lee and Jae-Kyung Jung of Chungbuk National University prepared the dibromopyridine 11 from the nitrile 10 (Adv. Synth. Catal. 2019, 361, 5458. DOI: 10.1002/adsc.201901002). Gaoxi Jiang of the Lanzhou Institute of Chemical Physics observed loss of fluoride in the conversion of 12 to the pyridine 13 (Chem. Sci. 2019, 10, 8812. DOI: 10.1039/C9SC03216A). Maxim G. Uchuskin of Perm State University and A. Stephen K. Hashmi of Heidelberg University and King Abdulaziz University converted 14 to an intermediate that they carried on to 15 (Chem. Sci. 2019, 10, 8583. DOI: 10.1039/C9SC02299F). Thomas R. Hoye of the University of Minnesota cyclized 16 in the presence of 17, leading to the adduct 18 (J. Am. Chem. Soc. 2019, 141, 19575. DOI: 10.1021/jacs.9b11243).

Magnus Rueping of RWTH Aachen and KAUST used a photocatalyst and white light to mediate the assembly of the indole 21 by the combination of 19 with 20 (Org. Chem. Front. 2019, 6, 2319. DOI: 10.1039/C9QO00206E). Xuegong She of Lanzhou University effected the oxidative cyclization of 22 to 23 (J. Org. Chem. 2019, 84, 14994. DOI: 10.1021/acs.joc.9b02462). Pei-Jun Cai of the China University of Mining and Technology and Bo Jiang of Jiangsu Normal University devised the cylization and nitration that converted 24 to 25 (Org. Chem. Front. 2019, 6, 2968. DOI: 10.1039/C9QO00715F). Hidetoshi Tokuyama of Tohoku University added cyanide to 26, leading to 27 (Org. Lett. 2019, 21, 6185. DOI: 10.1021/acs.orglett.9b01690).

The alkaloid suaveoline (30) was isolated from the trunk bark of the shrub Rauwolfia suaveolens of New Caledonia. En route to 30, Min Zhang of Chongqing University cyclized 28 to 29 (Angew. Chem. Int. Ed. 2019, 58, 6420. DOI: 10.1002/anie.201902155).

D. F. Taber, Org. Chem. Highlights 2020, June 15.