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Directed Fischer Indolization as an Approach to the Total Syntheses of (+)-Aspidospermidine and (−)-Tabersonine

Organic letters, v.19 no.22, 2017년, pp.6168 - 6171  

Kim, Joo-Young ,  Suhl, Chang-Heon ,  Lee, Joon-Ho ,  Cho, Cheon-Gyu

Abstract AI-Helper 아이콘AI-Helper

A conceptually new synthetic approach that provides general access to the aspidosperma alkaloids (+)-aspidospermidine and (−)-tabersonine was developed. This method is based on the regioselective indolization of an ene–hydrazide, which was obtained via a base-catalyzed intramolecular aza...

참고문헌 (29)

  1. The Alkaloids: Chemistry and Biology Blair L. M. 77 2017 

  2. O'Connor, Sarah E., Maresh, Justin J.. Chemistry and biology of monoterpene indole alkaloid biosynthesis. Natural product reports : a journal of current developments in bio-organic chemistry, vol.23, no.4, 532-547.

  3. The Alkaloids Saxton J. E. 51 1998 

  4. Pandey, Ganesh, Burugu, Shiva Kumar, Singh, Pushpendra. Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine. Organic letters, vol.18, no.7, 1558-1561.

  5. Tong, Shuo, Xu, Zhengren, Mamboury, Mathias, Wang, Qian, Zhu, Jieping. Aqueous Titanium Trichloride Promoted Reductive Cyclization of o‐Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine. Angewandte Chemie. international edition, vol.54, no.40, 11809-11812.

  6. Zhao, Senzhi, Andrade, Rodrigo B.. Domino Michael/Mannich/N-Alkylation Route to the Tetrahydrocarbazole Framework of Aspidosperma Alkaloids: Concise Total Syntheses of (−)-Aspidospermidine, (−)-Tabersonine, and (−)-Vincadifformine. Journal of the American Chemical Society, vol.135, no.36, 13334-13337.

  7. Li, Zeqian, Zhang, Shaoxiong, Wu, Shoutao, Shen, Xiaolei, Zou, Liwei, Wang, Fengqun, Li, Xiang, Peng, Fangzhi, Zhang, Hongbin, Shao, Zhihui. Enantioselective Palladium‐Catalyzed Decarboxylative Allylation of Carbazolones: Total Synthesis of (−)‐Aspidospermidine and (+)‐Kopsihainanine A. Angewandte Chemie. international edition, vol.52, no.15, 4117-4121.

  8. Kawano, Mizuki, Kiuchi, Takaaki, Negishi, Shoko, Tanaka, Hiroyuki, Hoshikawa, Takaya, Matsuo, Jun‐ichi, Ishibashi, Hiroyuki. Regioselective Inter‐ and Intramolecular Formal [4+2] Cycloaddition of Cyclobutanones with Indoles and Total Synthesis of (±)‐Aspidospermidine. Angewandte Chemie. international edition, vol.52, no.3, 906-910.

  9. Jones, Spencer B., Simmons, Bryon, Mastracchio, Anthony, MacMillan, David W. C.. Collective synthesis of natural products by means of organocascade catalysis. Nature, vol.475, no.7355, 183-188.

  10. Zhao, Senzhi, Andrade, Rodrigo B.. Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (−)-Aspidospermidine, (−)-Tabersonine, and (−)-Vincadifformine. Journal of organic chemistry, vol.82, no.1, 521-531.

  11. Kozmin, S. A., Iwama, T., Huang, Y., Rawal, V. H.. An Efficient Approach to Aspidosperma Alkaloids via [4 + 2] Cycloadditions of Aminosiloxydienes: Stereocontrolled Total Synthesis of (±)-Tabersonine. Gram-Scale Catalytic Asymmetric Syntheses of (+)-Tabersonine and (+)-16-Methoxytabersonine. Asymmetric Syntheses of (+)-Aspidospermidine and (−)-Quebrachamine. Journal of the American Chemical Society, vol.124, no.17, 4628-4641.

  12. Kuehne, Martin E., Podhorez, David E.. Studies in biomimetic alkaloid syntheses. 12. Enantioselective total syntheses of (-)- and (+)-vincadifformine and of (-)-tabersonine. Journal of organic chemistry, vol.50, no.7, 924-929.

  13. Ziegler, Frederick E., Bennett, Gregory B.. Claisen rearrangement in indole alkaloid synthesis. Total synthesis of (+-)-tabersonine. Journal of the American Chemical Society, vol.95, no.22, 7458-7464.

  14. Lim, Young-Kwan, Cho, Cheon-Gyu. Expedient synthesis of indoles from N-Boc arylhydrazines. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.45, no.9, 1857-1859.

  15. Zhan, Fuxu, Liang, Guangxin. Formation of Enehydrazine Intermediates through Coupling of Phenylhydrazines with Vinyl Halides: Entry into the Fischer Indole Synthesis. Angewandte Chemie. international edition, vol.52, no.4, 1266-1269.

  16. Lim, Byeong-Yun, Jung, Bo-Eun, Cho, Cheon-Gyu. Ene-hydrazide from Enol Triflate for the Regioselective Fischer Indole Synthesis. Organic letters, vol.16, no.17, 4492-4495.

  17. Horinouchi, Ryo, Kamei, Kouhei, Watanabe, Riki, Hieda, Nobushige, Tatsumi, Naoki, Nakano, Keiji, Ichikawa, Yoshiyasu, Kotsuki, Hiyoshizo. Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through the Primary Amine‐Catalyzed Michael Addition Reaction of α‐Substituted Cyclic Ketones at High Pressure. European journal of organic chemistry, vol.2015, no.20, 4457-4463.

  18. 10.1002/1521-3773(20020301)41:5<834::AID-ANIE834>3.0.CO;2-V 

  19. Wood, Michael R., Kim, June Y., Books, Kathy M.. A novel, one-step method for the conversion of primary alcohols into carbamate-protected amines. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.43, no.21, 3887-3890.

  20. Toyota, M., Wada, T., Ihara, M.. Total Syntheses of (−)-Methyl Atis-16-en-19-oate, (−)-Methyl Kaur-16-en-19-oate, and (−)-Methyl Trachyloban-19-oate by a Combination of Palladium-Catalyzed Cycloalkenylation and Homoallyl−Homoallyl Radical Rearrangement. Journal of organic chemistry, vol.65, no.15, 4565-4570.

  21. Muzart, J.. Synthesis of unsaturated carbonyl compounds via a chromium-mediated allylic oxidation by 70% tert.butylhydroperoxide. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.28, no.40, 4665-4668.

  22. Fukui, Yuki, Liu, Ping, Liu, Qiang, He, Zhi-Tao, Wu, Nuo-Yi, Tian, Ping, Lin, Guo-Qiang. Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C–H Activation. Journal of the American Chemical Society, vol.136, no.44, 15607-15614.

  23. Toczko, M. A., Heathcock, C. H.. Total Synthesis of (±)-Aspidospermidine. Journal of organic chemistry, vol.65, no.9, 2642-2645.

  24. Ishikawa, H., Elliott, G. I., Velcicky, J., Choi, Y., Boger, D. L.. Total Synthesis of (−)- and ent-(+)-Vindoline and Related Alkaloids. Journal of the American Chemical Society, vol.128, no.32, 10596-10612.

  25. Kobayashi, S., Ueda, T., Fukuyama, T.. An Efficient Total Synthesis of (-)-Vindoline. Synlett : accounts and rapid communications in synthetic organic chemistry, vol.2000, no.6, 883-886.

  26. Kuehne, Martin E., Okuniewicz, F. J., Kirkemo, C. L., Bohnert, J. C.. Studies in biomimetic alkaloid syntheses. 8. Total syntheses of the C-14 epimeric hydroxyvincadifformines, tabersonine, a (hydroxymethyl)-D-norvincadifformine and the C-20 epimeric pandolines. Journal of organic chemistry, vol.47, no.7, 1335-1343.

  27. Martinelli, M. J., Nayyar, N. K., Moher, E. D., Dhokte, U. P., Pawlak, J. M., Vaidyanathan, R.. Dibutyltin Oxide Catalyzed Selective Sulfonylation of &agr;-Chelatable Primary Alcohols. Organic letters, vol.1, no.3, 447-450.

  28. Elamparuthi, Elangovan, Fellay, Cindy, Neuburger, Markus, Gademann, Karl. Total Synthesis of Cyrneine A. Angewandte Chemie. international edition, vol.51, no.17, 4071-4073.

  29. Salmond, William G., Barta, Mary A., Havens, Jeffrey L.. Allylic oxidation with 3,5-dimethylpyrazole. Chromium trioxide complex steroidal .DELTA.5-7-ketones. Journal of organic chemistry, vol.43, no.10, 2057-2059.

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