Pyrrolizidine alkaloids. A concise entry to (-)-pyrrolam A

Tetrahedron Asymmetry

Volumn 8, Issue 4, 1997, Pages 515-518

  Giovenzana, Giovanni B ^a   Sisti, Massimo ^a   Palmisano, Giovanni ^b  

^a Dipartimento di Chimica Organica e Industriale   (Italy)

^b UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLAM A; PYRROLIZIDINE ALKALOID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DEHYDRATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031579466     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00010-4     Document Type: Article

References (17)

1. 1. Grote, R.; Zeeck, A.; Stümpfel, J.; Zähner, H. Liebigs Ann. Chem., 1990, 525.
2. 2. For recent reviews, see: Wrobel, J.T. "The Alkaloids" (Brossi A. Ed., vol. 26, 327; Academic Press, New York, 1985); Liddell, J.R. Nat. Prod. Rep. 1996, 13, 187.
3. 2. For recent reviews, see: Wrobel, J.T. "The Alkaloids" (Brossi A. Ed., vol. 26, 327; Academic Press, New York, 1985); Liddell, J.R. Nat. Prod. Rep. 1996, 13, 187.
4. 3. Mattock, A. R. "Chemistry and Toxicology of Pyrrolizidine Alkaloids", Academic Press, London, 1986.
5. 4. Cravotto, G.; Giovenzana, G.B.; Sisti, M.; Palmisano, G. Tetrahedron, 1996, 52, 13007.
6. AH value (13.3) of diethyl malonate has precluded any successful application as a proton donor in the Mitsunobu reactions. For a review, see: Hughes, D.L. Org. Prep. Proc. Int. 1996, 28, 129.
7. 6. (a) Buchschacher, P; Cassal, J.-M.; Fürst, A.; Meier, W. Helv. Chim. Acta 1977, 60, 2747;
8. (b) Tseng, C.C.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1977, 25, 29;
9. (c) Tsui, S.-K.; Wood, J.D. Can. J. Chem. 1979, 57, 1977.
10. 7. It has been shown that β-aminoalcohols can be converted into aziridines under the conditions of Mitsunobu reaction [Pfister, J.R. Synthesis 1984, 969; Freedman, J.; Vaal, M.J.; Huber, E.W. J. Org. Chem. 1991, 56, 670].
11. 7. It has been shown that β-aminoalcohols can be converted into aziridines under the conditions of Mitsunobu reaction [Pfister, J.R. Synthesis 1984, 969; Freedman, J.; Vaal, M.J.; Huber, E.W. J. Org. Chem. 1991, 56, 670].
12. 8. Pellegata, R.; Pinza, M.; Pifferi, G. Synthesis 1978, 614.
13. 9. Murray, A.; Proctor, G.R.; Murray, P.J. Tetrahedron Lett. 1995, 36, 291. For synthesis of (±)-7 see, also: Galinowski, A.; Reichard, A Ber. Dtsch.Chem. Ges. 1944, 77, 138; Danishefsky, S.; Dynak, J. J. Org. Chem. 1974, 39, 1979.
14. 9. Murray, A.; Proctor, G.R.; Murray, P.J. Tetrahedron Lett. 1995, 36, 291. For synthesis of (±)-7 see, also: Galinowski, A.; Reichard, A Ber. Dtsch.Chem. Ges. 1944, 77, 138; Danishefsky, S.; Dynak, J. J. Org. Chem. 1974, 39, 1979.
15. 9. Murray, A.; Proctor, G.R.; Murray, P.J. Tetrahedron Lett. 1995, 36, 291. For synthesis of (±)-7 see, also: Galinowski, A.; Reichard, A Ber. Dtsch.Chem. Ges. 1944, 77, 138; Danishefsky, S.; Dynak, J. J. Org. Chem. 1974, 39, 1979.
16. 10. Reich, H.J.; Renga, J.; Reich, I.L. J. Am. Chem. Soc. 1975, 97, 5434.
17. 11. The compound 1 was somewhat unstable; the characterization was made immediately after the preparation. The compound 1, and to a minor extent the compound 7, decomposed either at r.t. or at -20°C, giving rise to yellow mixtures, not analyzed.