Synthesis of pyrrolizidine alkaloids, (±)-trachelanthamidine, (±)-isoretronecanol, and (±)-supinidine, by means of an intramolecular carbenoid displacement (ICD) reaction

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 9, 1986, Pages 651-652

  Kametani, Tetsuji ^a   Yukawa, Hirotaka ^a   Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIZIDINE ALKALOID;

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; ISORETRONECANOL; NONHUMAN; PRELIMINARY COMMUNICATION; SUPINIDINE; THEORETICAL STUDY; TOXIN SYNTHESIS; TRACHELANTHAMIDINE;

EID: 0022897055     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39860000651     Document Type: Article

References (13)

1. T. Kametani, N. Kanaya, T. Mochizuki, and T. Honda, Heterocycles, 1982, 19, 1023;
2. T. Kametani, T. Honda, A. Nakayama, Y. Sakai, T. Mochizuki, and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1981, 2228;
3. T. Kametani, T. Honda, J. Sasaki, H. Terasawa, and K. Fukumoto, J. Chem. Soc., Perkin Trans., 1981, 1884;
4. T. Kametani, A. Nakayama, A. Itoh, and T. Honda, Heterocycles, 1983, 20, 2355.
5. The intramolecular carbon-carbon bond forming reactions of N-acyliminium ions have recently been reviewed, see W. N. Speckamp and H. Hiemstra, Tetrahedron, 1985, 41, 4367 and references cited therein.
6. ICD reaction has already been applied to the synthesis of a sesquiterpene, (±)-cuparene, T. Kametani, K. Kawamura, M. Tsubuki, and T. Honda, J. Chem. Soc., Chem. Commun., 1985, 1324.
7. B. M. Trost, Acc. Chem. Res., 1978, 11, 453;
8. E. Vedejs and G. A. Kraft, Tetrahedron, 1982, 38, 2857;
9. E. Vedejs, Acc. Chem. Res., 1984, 17, 358.
10. D. A. Burnett, J.-K. Choi, D. J. Hart, and Y.-M. Tsai. J. Am. Chem. Soc., 1984, 106, 8201.
11. S. A. Monti and S. D. Larsen, J. Org. Chem., 1978, 43, 2282.
12. G. A. Kraus and K. Neuenschwander, Tetrahedron Lett., 1980, 21, 3841.
13. D. J. Hart and T.-K. Yang, Tetrahedron Lett., 1982, 23, 2761.