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NTIS 바로가기Angewandte Chemie. international edition, v.46 no.13, 2007년, pp.2303 - 2305
Shin, In-Ji (Department of Chemistry, Hanyang University, 17 Haengdang-Dong, Sungdong-Ku, Seoul, Korea, Fax: (+82) 222-200-936) , Choi, Eun-Sil (Department of Chemistry, Hanyang University, 17 Haengdang-Dong, Sungdong-Ku, Seoul, Korea, Fax: (+82) 222-200-936) , Cho, Cheon-Gyu (Department of Chemistry, Hanyang University, 17 Haengdang-Dong, Sungdong-Ku, Seoul, Korea, Fax: (+82) 222-200-936)
Graphic AbstractAll essential functional groups in the natural product (±)-trans-dihydronarciclasine (1) were introduced with the correct relative configuration in a highly endo-selective Diels–Alder cycloaddition of 3,5-dibromo-2-pyrone with a styrene dienophile (see scheme). The total...
For reviews on the synthesis of these compounds see:
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Hudlicky, T., Rinner, U., Finn, K. J., Ghiviriga, I.. Reactions of Indole Derivatives with Oxiranes and Aziridines on Silica. Synthesis of &bgr;-Carbolin-1-one Mimic of Pancratistatin. Journal of organic chemistry, vol.70, no.9, 3490-3499.
Rinner, Uwe, Hudlicky, Tomas, Gordon, Heather, Pettit, George R.. A β-Carboline-1-one Mimic of the Anticancer Amaryllidaceae Constituent Pancratistatin: Synthesis and Biological Evaluation. Angewandte Chemie, vol.116, no.40, 5456-5460.
Rinner, Uwe, Hudlicky, Tomas, Gordon, Heather, Pettit, George R.. A β-Carboline-1-one Mimic of the Anticancer Amaryllidaceae Constituent Pancratistatin: Synthesis and Biological Evaluation. Angewandte Chemie. international edition, vol.43, no.40, 5342-5346.
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Compound4was synthesized chemically by the hydrogenation of narciclasine long before the disclosure of its biosynthesis.
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For a recent review and selected articles see:
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TAKEYA, Tetsuya, OHGUCHI, Akira, IKEYA, Tomoko, TOBINAGA, Seisho. Synthesis of a Simple (.+-.)-Dibenzocyclooctadiene Lignan, (.+-.)-Normethylgomisin A.. Chemical & pharmaceutical bulletin, vol.42, no.3, 677-679.
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Magnus, P., Sebhat, I. K.. Synthesis of the Antitumor Alkaloid (+)-Pancratistatin Using the &bgr;-Azidonation Reaction via a Prochiral 4-Arylcyclohexanone Derivative. Journal of the American Chemical Society, vol.120, no.21, 5341-5342.
Hudlicky, T., Rinner, U., Gonzalez, D., Akgun, H., Schilling, S., Siengalewicz, P., Martinot, T. A., Pettit, G. R.. Total Synthesis and Biological Evaluation of Amaryllidaceae Alkaloids: Narciclasine, ent-7-Deoxypancratistatin, Regioisomer of 7-Deoxypancratistatin, 10b-epi-Deoxypancratistatin, and Truncated Derivatives1. Journal of organic chemistry, vol.67, no.25, 8726-8743.
Banwell, Martin G., Bissett, Brett D., Busato, Stefan, Cowden, Cameron J., Hockless, David C. R., Holman, Jeffrey W., Read, Roger W., Wu, Angela W.. Trifluoromethanesulfonic anhydride–4-(N,N-dimethylamino)pyridine as a reagent combination for effecting Bischler–Napieraiski cyclisation under mild conditions: application to total syntheses of the Amaryllidaceae alkaloids N-methylcrinasiadine, anhydrolycorinone, hippadine and oxoassoanine. Journal of the Chemical Society, Chemical communications, vol.1995, no.24, 2551-2553.
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