Concise synthesis of the angular dihydrofuroquinoline alkaloids via cyclopropane opening in the presence of polyphosphoric acid

Synthetic Communications

Volumn 36, Issue 6, 2006, Pages 693-699

  Su, Jiangtao ^a   Xiong, Juan ^a   Liang, Shucai ^a   Qiu, Guofu ^a   Feng, Xichun ^a   Teng, Hanbing ^a   Wu, Lamei ^a   Hu, Xianming ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

Angluar; Cyclopropane; Furoquinolinone; Ring opening and closure

Indexed keywords

ALKALOID DERIVATIVE; CYCLOPROPANE; DIHYDROFUROQUINOLINE; POLYPHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; RING CLOSING METATHESIS; RING OPENING; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

EID: 32644466837     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500446530     Document Type: Article

References (15)

1. (a) Grundon, M. F. Nat. Prod. Rep. 1990, 7, 131;
2. (b) Scheuer, P. J. In Chemistry of Alkaloids; Pelletier, S. W. Ed.; Van Nostrand Reinhold: New York, 1970; Vol. 355;
3. (c) Openshaw, H. T. Alkaloids 1967, 9, 223;
4. (d) Michael, J. P. Nat. Prod. Rep. 1997, 14, 605;
5. (e) Moulis, C.; Wirasutisna, K. R.; Gleye, J.; Loiseau, P.; Stanislas, E.; Moretti, C. Phytochemistry 1983, 22, 2095.
6. (a) Michael, J. P. Nat. Prod. Rep. 2001, 18, 543-559;
7. (b) Le Bras. J. Antimicrob. Agents Chemother. 1994, 38, 1169;
8. (c) Wolters, B.; Eilert, U. Planta Med. 1981, 43, 166.
9. (a) Narasimhan, N. S.; Mall, R. S. Tetrahedron 1974, 30, 4153;
10. (b) Pirrung, M. C.; Blume, F. J. Org. Chem. 1994, 64, 3642;
11. (c) Suginome, H.; Kobayashi, K.; Itoh, M.; Seko, S. J. Org. Chem. 1990, 55, 4933;
12. (d) Senboku, H.; Takashima, M.; Suzuki, M.; Kobayashi, K.; Suginome, H. Tetrahedron 1996, 52, 6125;
13. (e) Lee, Y. R.; Kim, B. S.; Kweon, H. I. Tetrahedron 2000, 56, 3867.
14. (a) Kimpe, N. D.; Boeykens, M. J. Org. Chem. 1994, 59, 8215-8219;
15. (b) Salgado, A.; Huybrechts, T.; Kimpe, N. D. Tetrahedron 2001, 57, 2781-2786.