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Monday, June 26, 2023
Douglass F. Taber
University of Delaware

Functional Group Interconversion: The Hirose/Sunazuka Synthesis of Luminamicin

Qiao-qiao Teng and Ming Chen of Changzhou University showed that barium oxide is a strong enough base to doubly deuterate an alkyl nitrile 1, leading to 2 (Eur. J. Org. Chem. 2022, e202201218. DOI: 10.1002/ejoc.202201218). Hong-Hai Zhang of Nanjing Tech. University reported a complementary deuteration using a Pd catalyst (J. Org. Chem. 2022, 87, 16084. DOI: 10.1021/acs.joc.2c01654). Christian Wolf of Georgetown University showed that LiI converted an alkyl fluoride 3 to the alkyl iodide 4 (Synthesis 2022, 54, 4320. DOI: 10.1055/s-0041-1738383).

Takaaki Sato of Keio University assembled the enamide 7 by coupling the alkyne 5 with the dioxazolone 6 (Org. Lett. 2022, 24, 8662. DOI: 10.1021/acs.orglett.2c03497). Fraser F. Fleming of Drexel University showed that the formamide 9, prepared from the alkenyl iodide 8, could readily be dehydrated to the isonitrile (Org. Lett. 2022, 24, 8657. DOI: 10.1021/acs.orglett.2c03461). David E. Olson of the University of California, Davis used trimethylsilyl iodide followed by base to convert the carbamate 10 to the tertiary amine 11 (Org. Lett. 2022, 24, 6208. DOI: 10.1021/acs.orglett.2c02516). Takaaki Kamishima of the Genesis Research Institute used an Ir catalyst under a hydrogen atmosphere to rearrange the allylic alcohol 12 to the unsaturated aldehyde 13 (Eur. J. Org. Chem. 2022, e202201002. DOI: 10.1002/ejoc.202201002).

Changkun Li of Shanghai Jiao Tong University prepared the enol ester 15 by coupling the allene 14 with benzoic acid (Org. Chem. Front. 2022, 9, 6869. DOI: 10.1039/D2QO01153K). Serge Ruccolo and Gilmar Brito of Merck Rahway reported using electrolysis to regenerate ATP, driving the construction of the nucleoside 18 by the enzymatic coupling of the ribose derivative 16 with uracil 17 (J. Am. Chem. Soc. 2022, 144, 22582. DOI: 10.1021/jacs.2c08955).

Patrycja Żak of the Adam Mickiewicz University in Poznan used an N-heterocyclic carbene to catalyze the combination of the unsaturated aldehyde 19 with the thiol 20, to give the thioester 21 (Org. Chem. Front. 2022, 9, 4846. DOI: 10.1039/D2QO00678B). Fu-Min Zhang of Lanzhou University prepared the thioamide 24 by combining the nitrile 22 with the alkyl bromide 23 (Chem. Commun. 2022, 58, 11430. DOI: 10.1039/D2CC04210J). Keyume Ablajan of Xinjiang University showed that activation of the hydrazide 25 with iodine gave an intermediate that coupled with aniline, leading to the amide 26 (Synthesis 2022, 54, 4353. DOI: 10.1055/a-1838-9491). Jeffrey N. Johnston of Vanderbilt University fluorinated the nitroalkane 27, then combined that product with the N-hydroxy amine 28 to give the amide 29 (J. Am. Chem. Soc. 2022, 144, 16708. DOI: 10.1021/jacs.2c05986).

Luminamicin, an antiobiotic isolated from the culture broth of an actinomycete strain OMR-59, contains an unusual cyclic enol ether. Tomoyasu Hirose and Toshiaki Sunazuka of Kitasato University took advantage of this, preparing the enol ether 32 by coupling the alcohol 31 with the α-chloro sulfide 30 (J. Am. Chem. Soc. 2022, 144, 23148. DOI: 10.1021/jacs.2c10856).

D. F. Taber, Org. Chem. Highlights 2023, June 26.