Organic Chemistry Portal
Organic Chemistry Highlights

Monday, May 21, 2018
Douglass F. Taber
University of Delaware

Oxidation: The Maimone Synthesis of Majucin

Wei Zhang of Fudan University developed (Org. Biomol. Chem. 2017, 15, 9889. DOI: 10.1039/C7OB02329D) the oxidative cleavage of an alkene 1 to the amide 2. Brian M. Stoltz of Caltech showed (J. Am. Chem. Soc. 2017, 139, 13944. DOI: 10.1021/jacs.7b08496) that a Ru catalyst could effect both alkene migration and subsequent oxidative cleavage, converting 3 into 4.

Varinder K. Aggarwal of Bristol University devised (Science 2017, 357, 283. DOI: 10.1126/science.aan3679) a protocol for decarboxylative borylation, converting 5 into 6. Andreas Kirschning of the Leibniz Universität Hannover oxidized (Eur. J. Org. Chem. 2017, 6906. DOI: 10.1002/ejoc.201701349) the alcohol 7 to the adduct 9. Using an ionic liquid as a phase transfer catalyst, Agustín Ponzinibbio of the Universidad Nacional de La Plata effected (Tetrahedron Lett. 2017, 58, 3739. DOI: 10.1016/j.tetlet.2017.08.033) the in situ epoxidation of 10, leading to 11. Akbar Heydari of Tarbiat Modares University demonstrated (Synlett 2017, 28, 2315. DOI: 10.1055/s-0036-1589089) that a secondary amine 12 could be oxidized to the hydroxylamine 13.

Mekhman S. Yusubov of the Tomsk Polytechnic University, Professor Kirschning, and Viktor V. Zhdankin of the University of Minnesota, Duluth found (Adv. Synth. Catal. 2017, 359, 3207. DOI: 10.1002/adsc.201700776) that the combination of IBX-OTs with pyridine was an efficient reagent for oxidizing an alcohol 14 to the aldehyde 15. Secondary alcohols could also be oxidized to ketones. Lucia Tamborini of the University of Milan and Francesca Paradisi of the University of Nottingham developed (ChemCatChem 2017, 9, 3843. DOI: 10.1002/cctc.201701147) a flow-based system using an immobilized enzyme to convert the primary amine 16 to the aldehyde 17.

Timothy R. Newhouse of Yale University established (Angew. Chem. Int. Ed. 2017, 56, 13122. DOI: 10.1002/anie.201706893) a simple procedure for converting a carboxylic acid 18 to the α,β-unsaturated acid 19. Yuanyuan Xie of the Zhejian University of Technology coupled (Eur. J. Org. Chem. 2017, 7160. DOI: 10.1002/ejoc.201701411) the aldehyde 20 with N-OH phthalimide, leading to the activated ester 21. Kensuke Kiyokawa and Satoshi Minakata of Osaka University devised (J. Org. Chem. 2017, 82, 11711. DOI: 10.1021/acs.joc.7b01202) the Ritter-like coupling of 22 with acetonitrile to give the amide 23. Satyendra Kumar Pandey of Thapar University oxidized (Eur. J. Org. Chem. 2017, 6700. DOI: 10.1002/ejoc.201701289) the Henry adduct 24 to the ester 25.

The seco-prezizaane sesquiterpene majucin 28 was isolated from the Chinese flowering plant Illicium majus. En route to 28, Thomas J. Maimone of the University of California, Berkeley oxidized (J. Am. Chem. Soc. 2017, 139, 17783. DOI: 10.1021/jacs.7b11493) the cyclic ether 26 to the keto lactone 27.

D. F. Taber, Org. Chem. Highlights 2018, May 21.