Concise Access to a Model of the Marine Alkaloid Halicyclamine A through Macrocycle‐Forming Addition of a 5‐Aminopenta‐2,4‐dienal onto a 2,3‐Dihydropyridinium Salt
作者： Isabelle Sinigaglia , Tuan Minh Nguyen , Jean-Charles Wypych , Bernard Delpech , Christian Marazano
关键词: Halicyclamine A 、 Salt (chemistry) 、 Chemistry 、 Alkaloid 、 Organic chemistry 、 Biomimetic synthesis
摘要:
sci-hub.se 参考文章(23)
Jean‐Charles Wypych, Tuan Minh Nguyen, Philippe Nuhant, Michel Bénéchie, Christian Marazano, Further Insight from Model Experiments into a Possible Scenario Concerning the Origin of Manzamine Alkaloids Angewandte Chemie. ,vol. 47, pp. 5418- 5421 ,(2008) , 10.1002/ANIE.200800488
Blaine Harrison, Sunil Talapatra, Emil Lobkovsky, Jon Clardy, Phillip Crews, The structure and biogenetic origin of (-) halicyclamine B from a Xestospongia sponge Tetrahedron Letters. ,vol. 37, pp. 9151- 9154 ,(1996) , 10.1016/S0040-4039(96)02165-X
Alexander Kaiser, Xavier Billot, Alice Gateau-Olesker, Christian Marazano, Bhupesh C. Das, Selective Entry to the Dimeric or Oligomeric Pyridinium Sponge Macrocycles via Aminopentadienal Derivatives. Possible Biogenetic Relevance with Manzamine Alkaloids Journal of the American Chemical Society. ,vol. 120, pp. 8026- 8034 ,(1998) , 10.1021/JA9805369
Laurent Gil, Alice Gateau-Olesker, Christian Marazano, Bhupesh C. Das, 3-Alkyl 1,6-dihydropyridines from 3-alkyl 5,6-dihydro-pyridinium salts. Implications in the biosynthesis of some macrocyclic marine alkaloids Tetrahedron Letters. ,vol. 36, pp. 707- 710 ,(1995) , 10.1016/0040-4039(94)02339-D
Masayoshi Arai, Mari Sobou, Catherine Vilchéze, Anthony Baughn, Hiroyuki Hashizume, Patamaporn Pruksakorn, Shunsuke Ishida, Makoto Matsumoto, William R. Jacobs, Motomasa Kobayashi, Halicyclamine A, a marine spongean alkaloid as a lead for anti-tuberculosis agent Bioorganic & Medicinal Chemistry. ,vol. 16, pp. 6732- 6736 ,(2008) , 10.1016/J.BMC.2008.05.061
Jean-Charles Wypych, Tuan Minh Nguyen, Michel Bénéchie, Christian Marazano, Reaction of aldimine anions with vinamidinium chloride: three-component access to 3-alkylpyridines and 3-alkylpyridinium salts and access to 2-alkyl glutaconaldehyde derivatives. Journal of Organic Chemistry. ,vol. 73, pp. 1169- 1172 ,(2008) , 10.1021/JO702311K
David B. C. Martin, Christopher D. Vanderwal, Efficient Access to the Core of the Strychnos, Aspidosperma and Iboga Alkaloids. A Short Synthesis of Norfluorocurarine Journal of the American Chemical Society. ,vol. 131, pp. 3472- 3473 ,(2009) , 10.1021/JA900640V
Philippe Nuhant, Sanjay B. Raikar, Jean-Charles Wypych, Bernard Delpech, Christian Marazano, Enhancement of 5-aminopenta-2,4-dienals electrophilicity via activation by O,N-bistrifluoroacetylation. application to an N-acyl Pictet-Spengler reaction. Journal of Organic Chemistry. ,vol. 74, pp. 9413- 9421 ,(2009) , 10.1021/JO9019545
Shigeki Matsunaga, Yoshinari Miyata, Rob W. M. van Soest, Nobuhiro Fusetani, Tetradehydrohalicyclamine A and 22-hydroxyhalicyclamine A, new cytotoxic bis-piperidine alkaloids from a marine sponge Amphimedon sp. Journal of Natural Products. ,vol. 67, pp. 1758- 1760 ,(2004) , 10.1021/NP049824A
Richard J. Clark, Kim L. Field, Romila D. Charan, Mary J. Garson, M. Brereton, Anthony C. Willis, THE HALICLONACYCLAMINES, CYTOTOXIC TERTIARY ALKALOIDS FROM THE TROPICAL MARINE SPONGE HALICLONA SP. Tetrahedron. ,vol. 54, pp. 8811- 8826 ,(1998) , 10.1016/S0040-4020(98)00473-6