An unexpected aziridination/rearrangement/oxidation tandem reaction leading to the total synthesis of (−)-mersicarpine
作者： Yun Zhang , Yibin Xue , Tuoping Luo
DOI: 10.1016/J.TET.2016.11.049
关键词:
摘要: With the aim to synthesize anti-mitotic natural product (−)-rhazinal, we proposed a strategy based on dearomative intramolecular [3+2] cycloaddition between alkyl azide and indole, followed by rearrangement furnish featured tetracyclic framework. During reaction condition screening, accidentally encountered tandem cycloaddition/rearrangement/oxidation reaction, which enabled synthesis of another alkaloid, (−)-mersicarpine, in four steps with 35% overall yield from reported intermediate. The cycloaddition/rearrangement disclosed herein could provide method for other structurally intriguing alkaloids.
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A. Banerji, P.L. Majumder, A. Chatterjee, Occurrence of geissoschizine and other minor biogenetically related alkaloids in Rhazya stricta Phytochemistry. ,vol. 9, pp. 1491- 1493 ,(1970) , 10.1016/S0031-9422(00)85265-6
Horst H. A. Linde, Die Alkaloide aus Melodinus australis (F. MUELLER) PIERRE (Apocynaceae) Helvetica Chimica Acta. ,vol. 48, pp. 1822- 1842 ,(1965) , 10.1002/HLCA.19650480803
Rosana Álvarez, Claudio Martínez, Youssef Madich, J Gabriel Denis, José M Aurrecoechea, Ángel R de Lera, None, A General Synthesis of Alkenyl-Substituted Benzofurans, Indoles, and Isoquinolones by Cascade Palladium-Catalyzed Heterocyclization/Oxidative Heck Coupling Chemistry: A European Journal. ,vol. 16, pp. 12746- 12753 ,(2010) , 10.1002/CHEM.201001535
Martin G. Banwell, David W. Lupton, Anthony C. Willis, Application of the Palladium(0)-Catalyzed Ullmann Cross-Coupling Reaction in a Total Synthesis of (±)-Aspidospermidine and thus Representing an Approach to the Lower Hemisphere of the Binary Indole - Indoline Alkaloid Vinblastine Australian Journal of Chemistry. ,vol. 58, pp. 722- 737 ,(2005) , 10.1071/CH05181
Bruno David, Thierry Sévenet, Michel Morgat, Daniel Guénard, André Moisand, Yvette Tollon, Odile Thoison, Michel Wright, Rhazinilam mimics the cellular effects of taxol by different mechanisms of action Cytoskeleton. ,vol. 28, pp. 317- 326 ,(1994) , 10.1002/CM.970280405
Alexey Kuznetsov, Anton V. Gulevich, Donald J. Wink, Vladimir Gevorgyan, A New Reactivity Mode for the Diazo Group: Diastereoselective 1,3‐Aminoalkylation Reaction of β‐Amino‐α‐Diazoesters To Give Triazolines Angewandte Chemie. ,vol. 53, pp. 9021- 9025 ,(2014) , 10.1002/ANIE.201404352
Toh-Seok Kam, G Subramaniam, Kuan-Hon Lim, Yeun-Mun Choo, Mersicarpine, an unusual tetracyclic dihydroindole alkaloid incorporating a seven-membered imine ring Tetrahedron Letters. ,vol. 45, pp. 5995- 5998 ,(2004) , 10.1016/J.TETLET.2004.06.039
Maria C. DiPoto, Russell P. Hughes, Jimmy Wu, Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations – New Method for the Synthesis of Pyrroloindolines Journal of the American Chemical Society. ,vol. 137, pp. 14861- 14864 ,(2015) , 10.1021/JACS.5B10221
Wenzhi Ji, Licheng Yao, Xuebin Liao, Access to the Pyrroloindoline Core via [3 + 2] Annulation as well as the Application in the Synthetic Approach to (±)-Minfiensine Organic Letters. ,vol. 18, pp. 628- 630 ,(2016) , 10.1021/ACS.ORGLETT.5B03421
Zhuo Chai, You-Min Zhu, Pei-Jun Yang, Shaoyin Wang, Shaowu Wang, Zhen Liu, Gaosheng Yang, Copper(I)-Catalyzed Kinetic Resolution of N-Sulfonylaziridines with Indoles: Efficient Construction of Pyrroloindolines. Journal of the American Chemical Society. ,vol. 137, pp. 10088- 10091 ,(2015) , 10.1021/JACS.5B05820