C-H Functionalization: The Poulsen Synthesis of Strongylophorine-2

Organic Chemistry Portal - Guigen Li of Texas Tech University and Haibo Ge of IUPUI used (J. Am. Chem. Soc. 2016, 138, 12775. DOI: 10.1021/jacs.6b08478) catalytic 3-aminopropanoic acid to prepare 3 by the distal arylation of 1 with 2.

Guigen Li of Texas Tech University and Haibo Ge of IUPUI used (J. Am. Chem. Soc. 2016, 138, 12775. DOI: 10.1021/jacs.6b08478) catalytic 3-aminopropanoic acid to prepare 3 by the distal arylation of 1 with 2. Guangbin Dong of the University of Texas (Angew. Chem. Int. Ed. 2016, 55, 9084. DOI: 10.1002/anie.201604268) and Jin-Quan Yu of Scripps/La Jolla (J. Am. Chem. Soc. 2016, 138, 14554. DOI: 10.1021/jacs.6b09653) employed an inverted strategy, arylating 4 to 6 by way of imine formation with 5. Bing-Feng Shi of Zhejiang University observed (J. Am. Chem. Soc. 2016, 138, 10750. DOI: 10.1021/jacs.6b05978) high regioselectivity in the alkenylation of 7 with 8 to give 9. Robert R. Knowles of Princeton University (Nature 2016, 539, 268. DOI: 10.1038/nature19811) and Tomislav Rovis of Colorado State University (Nature 2016, 539, 272. DOI: 10.1038/nature19810) developed a photochemically-activated Ir catalyst to effect distal H-atom removal from 10, leading to a free radical intermediate that added to 11 to give 12.

Read the story here.