Organic Chemistry Portal
Organic Chemistry Highlights

Monday, July 13, 2020
Douglass F. Taber
University of Delaware

Enantioselective Synthesis of Alcohols and Amines: The Menche Synthesis of Tuscoron D

Yuanyuan Liu of East China Normal University and Zhi-Min Chen of Shanghai Jiao Tong University employed the Denmark BINAM-derived selenide to catalyze the cyclization of 1 with 2 to give the lactone 3 (Chem. Eur. J. 2019, 25, 15411. DOI: 10.1002/chem.201904028). Sergey V. Pronin of the University of California, Irvine used a Co catalyst with 5 to prepare the epoxide 6 from the alcohol 4 (J. Am. Chem. Soc. 2019, 141, 17527. DOI: 10.1021/jacs.9b10645).

Hongxin Liu and Jun Jiang of Wenzhou University assembled 9 by adding 8 to the aldehyde 7 (Org. Lett. 2019, 21, 6684. DOI: 10.1021/acs.orglett.9b02297). Wei He of the Fourth Military Medical University achieved high ee in the preparation of 12 by the addition of nitroethane 11 to the aldehyde 10 (Tetrahedron 2019, 75, 130469. DOI: 10.1016/j.tet.2019.130469).

Xiaodan Zhao of Sun Yat-Sen University used a selenide to mediate the addition of 14 to 13, leading to 15 (ACS Catal. 2019, 9, 6896. DOI: 10.1021/acscatal.9b01900). Junliang Zhang of Fudan University used a cyclic phosphine to direct the preparation of 18 by the addition of 17 to 16 (Chem. Sci. 2019, 10, 10510. DOI: 10.1039/C9SC04073K). Scott J. Miller of Yale University and Robert R. Knowles of Princeton University showed that under the influence of a peptide thiol catalyst and with photochemical stimulation, racemic 19 could be epimerized into enantiomerically-enriched 20 (Science 2019, 366, 364. DOI: 10.1126/science.aay2204). Shou-Fei Zhu and Qi-Lin Zhou of Nankai University achieved high ee in the insertion of the carbene derived from 21 into the N-H of 22, leading to 23 (Science 2019, 366, 990. DOI: 10.1126/science.aaw9939). Xiaohua Liu of Sichuan University described a parallel investigation (not illustrated) (Chem. Sci. 2019, 10, 10305. DOI: 10.1039/C9SC03354H).

Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry devised a Ni catalyst for the preparation of 25 by the addition of acetonitrile to 24 (Org. Lett. 2019, 21, 8187. DOI: 10.1021/acs.orglett.9b02821). Olivier Baudoin of the University of Basel metalated 26, then coupled the derived organozinc with 27 to give 28 (Nature Catal. 2019, 2, 882. DOI: 10.1038/s41929-019-0336-1). Hsuyueh-Liang Wu of the National Taiwan Normal University showed that 30 could be prepared in high ee by conjugate addition to 29 (Org. Lett. 2019, 21, 9468. DOI: 10.1021/acs.orglett.9b03666). Chi Wai Cheung and Jun-An Ma of Tianjin University used a BINOL-derived phosphoric acid to assemble 33 by the Mannich condensation of 32 with 31 (Org. Lett. 2019, 21, 8419. DOI: 10.1021/acs.orglett.9b03181).

Tuscoron D (36) was isolated from a culture of the myxobacterium Sorangium cellulosum. In the course of a synthesis of 36, Dirk Menche of the Universitšt Bonn effected the conversion of the epoxide 34 to the alkyne 35 (Angew. Chem. Int. Ed. 2019, 58, 13019. DOI: 10.1002/anie.201906166).

D. F. Taber, Org. Chem. Highlights 2020, July 13.