Total Synthesis of Arcutinidine

In this episode we analyze the total synthesis of arcutinidine developed by the Li lab and compare it to recent syntheses completed by the Sarpong and Qin labs.

DOI: 10.1021/jacs.9b05818

References:

Zhou, S.; Xia, K.; Leng, X.; Li, A. Asymmetric Total Synthesis of Arcutinidine, Arcutinine, and Arcutine. J. Am. Chem. Soc. 2019.

Owens, K. R.; McCowen, S.; Blackford, K. A.; Ueno, S.; Hirooka, Y.; Weber, M.; Sarpong, R. Total Synthesis of the Diterpenoid Alkaloid Arcutinidine Using a Strategy Inspired by Chemical Network Analysis. J. Am. Chem. Soc. 2019.

Nie, W.; Gong, J.; Chen, Z.; Liu, J.; Tian, D.; Song, H.; Liu, X.-Y.; Qin, Y. Enantioselective Total Synthesis of (−)-Arcutinine. J. Am. Chem. Soc. 2019, 141 (24), 9712–9718.

Atta-ur-Rahman; Iqbal Choudhary, M.; Atta-ur-Rahman; Iqbal Choudhary, M.; Atta-ur-Rahman; Iqbal Choudhary, M. Diterpenoid and Steroidal Alkaloids. Nat. Prod. Rep. 1999, 16 (5), 619–635.

Wang, F.-P.; Chen, Q.-H.; Liu, X.-Y. Diterpenoid Alkaloids. Nat. Prod. Rep. 2010, 27 (4), 529.

Li, J.; Zhang, W.; Zhang, F.; Chen, Y.; Li, A. Total Synthesis of Longeracinphyllin A. J. Am. Chem. Soc. 2017, 139 (42), 14893–14896.

Zhou, S.; Guo, R.; Yang, P.; Li, A. Total Synthesis of Septedine and 7 Deoxyseptedine. J. Am. Chem. Soc. 2018, 140 (29), 9025–9029.

Ohnuma, T.; Oishi, T.; Ban, Y. Synthetic Entry to the Hexacyclic Aspidosperma Alkaloids. Total Synthesis of (±)-4-Hydroxyaspidofractinine. J. Chem. Soc., Chem. Commun. 1973, No. 9, 301–302.

Okamura, H.; Iwagawa, T.; Nakatani, M. A Base Catalyzed Diels-Alder Reaction of 3-Hydroxy-2-Pyrone. Tetrahedron Lett. 1995, 36 (33), 5939–5942.

Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. A Greatly Improved Procedure for Ruthenium Tetroxide Catalyzed Oxidations of Organic Compounds. J. Org. Chem. 1981, 46 (19), 3936–3938.

Hamlin, A. M.; Lapointe, D.; Owens, K.; Sarpong, R. Studies on C 20 -Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine
Skeleton. J. Org. Chem. 2014, 79 (15), 6783–6800.

Marth, C. J.; Gallego, G. M.; Lee, J. C.; Lebold, T. P.; Kulyk, S.; Kou, K. G. M.; Qin, J.; Lilien, R.; Sarpong, R. Network-Analysis-Guided Synthesis of Weisaconitine D and Liljestrandinine. Nature 2015, 528 (7583), 493–498.