Total synthesis of (±)-erythravine based on ring closing dienyne metathesis

Tetrahedron Letters

Volumn 44, Issue 44, 2003, Pages 8047-8049

  Fukumoto, Hironori ^a   Esumi, Tomoyuki ^a   Ishihara, Jun ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Erythravine; Erythrina alkaloid; Ring closing dienyne metathesis; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; ALKENE; ALKYNE DERIVATIVE; DIENYNE; ERYTHRAVINE; HOMOVERATRYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0141571034     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.059     Document Type: Article

References (20)

1. For a review of the erythrina alkaloids, see: Tsuda, Y.; Sano, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996,; Vol. 48, pp 249-337.
2. For the synthetic methodologies developed recently, see: (a) Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144-1155; (b) Toda, J.; Niimura, Y.; Takeda, K.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 906; (c) Rigby, J. H.; Deur, C.; Heeg, M. J. Tetrahedron Lett. 1999, 40, 6887-6890; (d) Kawasaki, T.; Onoda, N.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2001, 42, 8003-8006; (e) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamaru, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312-318.
3. For the synthetic methodologies developed recently, see: (a) Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144-1155; (b) Toda, J.; Niimura, Y.; Takeda, K.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 906; (c) Rigby, J. H.; Deur, C.; Heeg, M. J. Tetrahedron Lett. 1999, 40, 6887-6890; (d) Kawasaki, T.; Onoda, N.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2001, 42, 8003-8006; (e) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamaru, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312-318.
4. For the synthetic methodologies developed recently, see: (a) Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144-1155; (b) Toda, J.; Niimura, Y.; Takeda, K.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 906; (c) Rigby, J. H.; Deur, C.; Heeg, M. J. Tetrahedron Lett. 1999, 40, 6887-6890; (d) Kawasaki, T.; Onoda, N.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2001, 42, 8003-8006; (e) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamaru, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312-318.
5. For the synthetic methodologies developed recently, see: (a) Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144-1155; (b) Toda, J.; Niimura, Y.; Takeda, K.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 906; (c) Rigby, J. H.; Deur, C.; Heeg, M. J. Tetrahedron Lett. 1999, 40, 6887-6890; (d) Kawasaki, T.; Onoda, N.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2001, 42, 8003-8006; (e) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamaru, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312-318.
6. For the synthetic methodologies developed recently, see: (a) Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144-1155; (b) Toda, J.; Niimura, Y.; Takeda, K.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 906; (c) Rigby, J. H.; Deur, C.; Heeg, M. J. Tetrahedron Lett. 1999, 40, 6887-6890; (d) Kawasaki, T.; Onoda, N.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2001, 42, 8003-8006; (e) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamaru, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312-318.
7. Kim S.-H., Zuercher W.J., Bowden N.B., Grubbs R.H. J. Org. Chem. 61:1996;1073-1081.
8. For a related dieneyne RCM, see: Huang J., Xiong H., Hsung R.P., Rameshkumar C., Mulder J.A., Grebe T.P. Org. Lett. 4:2002;2417-2420.
9. Shimizu K., Takimoto M., Mori M. Org. Lett. 5:2003;2323-2325.
10. 3=Me) to erythravine was reported: Sarragiotto M.H., da Costa P.A., Marsaioli A.J. Heterocycles. 22:1984;453-456.
11. This work was presented at the 32nd Congress of Heterocyclic Chemistry, Tokushima, Japan, December 4-6, 2002.
12. Varcauteren J., Lavaut C., Levy J., Massiot G. J. Org. Chem. 49:1984;2278-2279.
13. Müller S., Liepold B., Roth G.J., Bestmann H.J. Synlett. 1996;521-522.
14. Schwab P., France M.B., Ziller J.W., Grubbs R.H. Angew. Chem., Int. Ed. Engl. 34:1995;2039-2041.
15. Schwab P., Grubbs R.H., Ziller J.W. J. Am. Chem. Soc. 118:1996;100-110.
16. Scholl M., Ding S., Lee C.W., Grubbs R.H. Org. Lett. 1:1999;953-956.
17. Fu G.C., Nguyen S.T., Grubbs R.H. J. Am. Chem. Soc. 115:1993;9856-9857.
18. In this regard, Mori et al. observed that the RCM reaction of the corresponding hydrochloride successfully occurred at room temperature; see Ref. 5.
19. 3: 299.1517, found: 299.1521.
20. Millington D.S., Steinman D.H., Rinehert K.L. Jr. J. Am. Chem. Soc. 96:1974;1909-1917.