Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide

Organic Letters

Volumn 3, Issue 9, 2001, Pages 1367-1369

  Goti, Andrea ^a   Cacciarini, Martina ^a   Cardona, Francesca ^a   Cordero, Franca M ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; HASTANECINE; MALIC ACID; MALIC ACID DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIZIDINE ALKALOID; ROSMARINECINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKALOIDS; MAGNETIC RESONANCE SPECTROSCOPY; MALATES; MOLECULAR STRUCTURE; PYRROLES; PYRROLIZIDINE ALKALOIDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035799890     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015747o     Document Type: Article

References (25)

1. Goti, A.; Cicchi, S.; Cacciarini, M.; Cardona, F.; Fedi, V.; Brandi, A. Eur. J. Org. Chem. 2000, 3633.
2. Hartmann, T.; Witte L. In Alkaloids: Chemical & Biological Perspectives, Vol. 9; Pelletier, S. W., Ed.; Pergamon: Oxford, 1995; p 155.
3. (a) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Client. Soc. 1983, 105, 4096.
4. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266.
5. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
6. D-Malic acid is ca. 30 times as expensive as its L-enantiomer.
7. Zilkha, A.; Bachi, M. J. Org. Chem. 1959, 24, 1096.
8. (a) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem. 1997, 62, 3119.
9. (b) Goti, A.; Cacciarini, M.; Cardona, F.; Brandi, A. Tetrahedron Lett. 1999, 40, 2853.
10. For reviews on the Mitsunobu reaction, see: (a) Mitsunobu, O. Synthesis 1981, 1.
11. (b) Castro, B. R. Org. React. 1983, 29, 1.
12. (c) Hughes, D. L. Org. React. 1992, 42, 335.
13. Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; De Sarlo, F. Tetrahedron Lett. 1990, 31, 3351.
14. (a) LeBel, N. A.; Post, M. E.; Whang, J. J. J. Am. Chem. Soc. 1964, 86, 3759.
15. (b) Huisgen, R.; Hauck, H.; Grashey, R.; Seidl, H. Chem. Ber. 1968, 101, 2559.
16. Tufariello, J. J.; Meckler, H.; Senaratne, K. P. A. Tetrahedron 1985, 41, 3447.
17. Dhavale, D. D.; Gentilucci, L.; Piazza, M. G.; Trombini, C. Liebigs Ann. Chem. 1992, 1289.
18. Tice, C. M.; Ganem, B. J. Org. Chem. 1983, 48, 5048.
19. DeShong, P.; Leginus, J. M. J. Am. Chem. Soc. 1983, 105, 1686.
20. Cordero, F. M.; Gensini, M.; Goti, A.; Brandi, A. Org. Lett. 2000, 2, 2475.
21. 7 Studies are in progress in order to ascertain the origin and mechanism of this racemization process.
22. (a) Murahashi, S.-I.; Shiota, T. Tetrahedron Lett. 1987, 28, 6469.
23. (b) Padwa, A.; Koehler, K. F. J. Chem. Soc., Chem. Commun. 1986, 789.
24. (a) Tufariello, J. J.; Mullen, G. B.; Tegeler, J. J.; Trybulski, E. J.; Chun Wong, S.; Asrof Ali, Sk. J. Am. Chem. Soc. 1979, 101, 2435.
25. (b) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B. J. Am. Chem. Soc. 1999, 121, 4900.