Studies towards the Leucetta‐Derived Alkaloids Spirocalcaridine A and B – Possible Biosynthetic Implications
作者： Panduka B. Koswatta , Jayanta Das , Muhammed Yousufuddin , Carl J. Lovely
关键词:
摘要: An exploration of an abiotic approach to spirocalcaridines A and B is described centered on electrophile-induced dearomatizing spirocyclization aryl enyne derivatives. Elaboration the α-iodoenone via Ullmann-like, copper-catalyzed amidation provided a formamide which upon treatment with methylamine undergoes dienol-arene rearrangement, providing corresponding kealiinine-like framework. This observation suggests possible biosynthetic links between naphthimidazole group Leucetta alkaloids.
sci-hub.se 参考文章(33)
Rahman Hosseinzadeh, Yaghoub Sarrafi, Maryam Mohadjerani, Fatemeh Mohammadpourmir, Copper-catalyzed arylation of phenylurea using KF/Al2O3 Tetrahedron Letters. ,vol. 49, pp. 840- 843 ,(2008) , 10.1016/J.TETLET.2007.11.180
Nan Zheng, Stephen L. Buchwald, Copper-Catalyzed Regiospecific Synthesis of N-Alkylbenzimidazoles Organic Letters. ,vol. 9, pp. 4749- 4751 ,(2007) , 10.1021/OL7020737
Maurice Shamma, Héléne Guinaudeau, Biogenetic pathways for the aporphinoid alkaloids Tetrahedron. ,vol. 40, pp. 4795- 4822 ,(1984) , 10.1016/S0040-4020(01)91314-6
Anna Rosiak, Wolfgang Frey, Jens Christoffers, Synthesis of Tetrahydropyran‐4‐ones and Thiopyran‐4‐ones from Donor‐Substituted α‐Bromostyrene Derivatives European Journal of Organic Chemistry. ,vol. 2006, pp. 4044- 4054 ,(2006) , 10.1002/EJOC.200600372
Weimin Lin, Anuradha Gupta, Kyung Hee Kim, David Mendel, Marvin J. Miller, Syntheses of New Spirocarbocyclic Nucleoside Analogs Using Iminonitroso Diels-Alder Reactions Organic Letters. ,vol. 11, pp. 449- 452 ,(2009) , 10.1021/OL802553G
Ru Angelie Edrada, Chad C. Stessman, Phillip Crews, Uniquely modified imidazole alkaloids from a calcareous Leucetta sponge. Journal of Natural Products. ,vol. 66, pp. 939- 942 ,(2003) , 10.1021/NP020503D
Rhone K. Akee, Tony R. Carroll, Wesley Y. Yoshida, Paul J. Scheuer, Thomas J. Stout, Jon Clardy, Two imidazole alkaloids from a sponge Journal of Organic Chemistry. ,vol. 55, pp. 1944- 1946 ,(1990) , 10.1021/JO00293A048
Yumiko Nagasawa, Hikaru Kato, Henki Rotinsulu, Remy E.P. Mangindaan, Nicole J. de Voogd, Sachiko Tsukamoto, Spironaamidine, a new spiroquinone-containing alkaloid from the marine sponge Leucetta microraphis Tetrahedron Letters. ,vol. 52, pp. 5342- 5344 ,(2011) , 10.1016/J.TETLET.2011.08.026
Lei Jiang, Gabriel E. Job, Artis Klapars, Stephen L. Buchwald, Copper-catalyzed coupling of amides and carbamates with vinyl halides. Organic Letters. ,vol. 5, pp. 3667- 3669 ,(2003) , 10.1021/OL035355C
Heather M. Lima, Beatriz J. Garcia-Barboza, Nicole N. Khatibi, Carl J. Lovely, Total syntheses of isonaamine C and isonaamidine E Tetrahedron Letters. ,vol. 52, pp. 5725- 5727 ,(2011) , 10.1016/J.TETLET.2011.08.030