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Monday, December 9, 2019
Douglass F. Taber
University of Delaware

Metal-Mediated C-C Ring Construction: The Saicic/Bihelovic Synthesis of Platensimycin

Nicolai Cramer of the Ecole Polytechnique Fédérale de Lausanne devised a strategy for assembling the cyclopropane 4 by combining 1 first with 2, then with 3 (Chem. Sci. 2019, 10, 2773. ). Tomislav Rovis of Columbia University described related results (J. Am. Chem. Soc. 2019, 141, 6807. ). Xiaohua Liu and Xiaoming Feng of Sichuan University prepared 7 by adding 5 to 6 (Chem. Eur. J. 2018, 24, 19361. ). Mu-Hyun Baik of KAIST and Tehshik P. Yoon of the University of Wisconsin reported a parallel investigation (J. Am. Chem. Soc. 2019, 141, 9543. ).

Corinna S. Schindler of the University of Michigan found conditions for the cyclization of 8 to 9 (carbonyl-alkene metathesis) (J. Am. Chem. Soc. 2019, 141, 1690. ). Vy M. Dong of the University of California, Irvine reported the conversion of the racemic aldehyde 10 to the cyclopentanol 11 in high ee (Angew. Chem. Int. Ed. 2019, 58, 4705. ). Gang Zhao of the Shanghai Institute of Organic Chemistry prepared 14 by adding 13 to 12 (Tetrahedron 2019, 75, 2706. ). Jan Vesely of Charles University assembled 17 by combining 15 with 16 (Chem. Commun. 2019, 55, 3829. ).

Phil S. Baran of Scripps/La Jolla devised a practical protocol for electrochemical Birch reduction, converting 18 to 19 (Science 2019, 363, 838. ). Lukas S. Goossen of the Ruhr-Universität Bochum and Jin-Quan Yu, also of Scripps/La Jolla, established a strategy for coupling 20 with 21 to give either diastereomer of 22 in high ee (Chem. Eur. J. 2019, 25, 8503. ). Stephen P. Fletcher of the University of Oxford prepared 25 by coupling 24, prepared from the corresponding alkene, with the prochiral 23 (Nature Commun. 2019, 10, 21. ). Yoshihiro Sato of Hokkaido University cyclized the racemic allene 26 selectively to 27 (Org. Lett. 2019, 21, 4120. ).

Paul J. Chirik of Princeton University prepared the cyclooctadiene 30 by combining the diene 28 with the diene 29 (J. Am. Chem. Soc. 2019, 141, 8557. ). Xiang Wu of the Hefei University of Technology used a Pd catalyst to cyclize 31, then couple that intermediate with 32, leading to 33 (Chem. Commun. 2019, 55, 3769. ).

Platensimycin (36), an antibiotic initially isolated from a strain of Streptomyces platensis, is in preclinical development for the treatment of MRSA. In the course of the preparation of a known intermediate in the total synthesis of 36, Radomir N. Saicic and Filip Bihelovic of the University of Belgrade devised the silver-mediated cyclization of 34 to 35 (Chem. Eur. J. 2019, 25, 4340. ).

D. F. Taber, Org. Chem. Highlights 2019, December 9.
URL: https://www.organic-chemistry.org/Highlights/2019/09December.shtm