Scalable total syntheses of (−)-hapalindole U and (+)-ambiguine H

作者: Thomas J. Maimone , Yoshihiro Ishihara , Phil S. Baran

DOI: 10.1016/J.TET.2014.11.010

关键词:

摘要: The Stigonemataceae family of cyanobacteria produces a class biogenetically related indole natural products that include hapalindoles and ambiguines. In this full account, practical route to the tetracyclic hapalindole is presented by way an eight-step, enantiospecific, protecting-group-free total synthesis (−)-hapalindole U features oxidative indole–enolate coupling. With gram-scale access U, first ambiguine alkaloid, (+)-ambiguine H, was completed via isonitrile-assisted prenylation followed photofragmentation cascade.

参考文章(87)
Nga Thanh Doan, Rodney W. Rickards, Jennifer M. Rothschild, Geoffrey D. Smith, Allelopathic actions of the alkaloid 12-epi-hapalindole E isonitrile and calothrixin A from cyanobacteria of the genera Fischerella and Calothrix Journal of Applied Phycology. ,vol. 12, pp. 409- 416 ,(2000) , 10.1023/A:1008170007044
Nicholas J. Turro, Modern Molecular Photochemistry ,(1978)
Shunyan Mo, Aleksej Krunic, Bernard D. Santarsiero, Scott G. Franzblau, Jimmy Orjala, Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua. Phytochemistry. ,vol. 71, pp. 2116- 2123 ,(2010) , 10.1016/J.PHYTOCHEM.2010.09.004
Jeremy M. Richter, Brandon W. Whitefield, Thomas J. Maimone, David W. Lin, M. Pilar Castroviejo, Phil S. Baran, Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: total synthesis of acremoauxin A and oxazinin 3. Journal of the American Chemical Society. ,vol. 129, pp. 12857- 12869 ,(2007) , 10.1021/JA074392M
Paul G. Becher, Simone Keller, Günther Jung, Roderich D. Süssmuth, Friedrich Jüttner, Insecticidal activity of 12-epi-hapalindole J isonitrile. Phytochemistry. ,vol. 68, pp. 2493- 2497 ,(2007) , 10.1016/J.PHYTOCHEM.2007.06.024
D. Klein, D. Daloze, J. C. Braekman, L. Hoffmann, V. Demoulin, New Hapalindoles from the Cyanophyte Hapalosiphon laingii Journal of Natural Products. ,vol. 58, pp. 1781- 1785 ,(1995) , 10.1021/NP50125A025
Alexander D. Huters, Kyle W. Quasdorf, Evan D. Styduhar, Neil K. Garg, Total Synthesis of (−)-N-Methylwelwitindolinone C Isothiocyanate Journal of the American Chemical Society. ,vol. 133, pp. 15797- 15799 ,(2011) , 10.1021/JA206538K
James A. MacKay, Raynauld L. Bishop, Viresh H. Rawal, Rapid Synthesis of theN-Methylwelwitindolinone Skeleton Organic Letters. ,vol. 7, pp. 3421- 3424 ,(2005) , 10.1021/OL051043T