Electrocyclization of β-arylvinyl ketenimines: Formal syntheses of the alkaloid from marine origin, 5,8-dihydro-7-methoxy-1,6-dimethylisoquinoline-5,8-dione, and 3-ethoxycarbonylrenierol

Synthesis

Volumn , Issue 8, 1997, Pages 963-966

  Molina, Pedro ^a   Vidal, Angel ^a   Tovar, Fulgencio ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 ETHOXYCARBONYLRENIEROL; 5,8 DIHYDRO 7 METHOXY 1,6 DIMETHYL 5,8 ISOQUINOLINEDIONE; ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DEMETHYLATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030772756     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1277     Document Type: Article

References (14)

1. McIntyre, D. E.; Faulkner, D. J.; Van Engen, D.; Clardy, J. Tetrahedron Lett. 1979, 20, 4163.
2. Kubo, A.; Nakahara, S.; Iwata, R.; Takahashi, K.; Arai, T. Tetrahedron Lett. 1980, 21, 3207.
3. McKee, T.; Ireland, C. M. J. Nat. Prod. 1987, 50, 754.
4. Frincke, J. M.; Faulkner, D. J. J. Am. Chem. Soc. 1982, 104, 265.
5. Take, Y.; Oogose, K.; Kubo, T.; Inouye, Y.; Nakamura, S.; Kitahara, Y.; Kubo, A. J. Antibiotics 1987, 40, 679. Inouye, Y.; Oogose, K.; Take, Y.; Kubo, T.; Nakamura, S. J. Antibiotics 1987, 40, 702. Take, Y.; Inouye, Y.; Nakamura, S.; Allaudeen, H. S.; Kubo, A. J. Antibiotics 1989, 42, 107.
6. Take, Y.; Oogose, K.; Kubo, T.; Inouye, Y.; Nakamura, S.; Kitahara, Y.; Kubo, A. J. Antibiotics 1987, 40, 679. Inouye, Y.; Oogose, K.; Take, Y.; Kubo, T.; Nakamura, S. J. Antibiotics 1987, 40, 702. Take, Y.; Inouye, Y.; Nakamura, S.; Allaudeen, H. S.; Kubo, A. J. Antibiotics 1989, 42, 107.
7. Take, Y.; Oogose, K.; Kubo, T.; Inouye, Y.; Nakamura, S.; Kitahara, Y.; Kubo, A. J. Antibiotics 1987, 40, 679. Inouye, Y.; Oogose, K.; Take, Y.; Kubo, T.; Nakamura, S. J. Antibiotics 1987, 40, 702. Take, Y.; Inouye, Y.; Nakamura, S.; Allaudeen, H. S.; Kubo, A. J. Antibiotics 1989, 42, 107.
8. Kubo, A.; Nakahara, S.; Inaba, K.; Kitahara, Y. Chem. Pharm. Bull. 1986, 34, 4056. Iyer, S.; Liebeskind, L. S. J. Am. Chem. Soc. 1987, 109, 2759.
9. Kubo, A.; Nakahara, S.; Inaba, K.; Kitahara, Y. Chem. Pharm. Bull. 1986, 34, 4056. Iyer, S.; Liebeskind, L. S. J. Am. Chem. Soc. 1987, 109, 2759.
10. Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197.
11. Molina, P.; Garcia-Zafra, S.; Fresneda, P. M. Synlett 1995, 43.
12. Molina, P.; Vidal, A.; Barquero, I. Synthesis 1996, 1199.
13. Matsuo, K.; Okumura, M.; Tanaka, K. Chem. Pharm. Bull. 1982, 30, 4170.
14. Valenti, F.; Pericás, M. A.; Serratosa, F. J. Org. Chem. 1990, 55, 395.