An efficient asymmetric synthesis of allo- and pseudo-7,8-dimethoxyberbane systems through tin-mediated three component coupling

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 443-449

  Haraguchi, Yoshikazu ^a   Kozima, Sinpei ^a   Yamaguchi, Ryohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIBENZO[A,G]QUINOLIZINE DERIVATIVE; QUINOLIZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030039873     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00027-4     Document Type: Article

References (14)

1. For a review: Bhakuni, D. S.; Jain, S. in "The Alkaloids", Brossi, A. Ed., Academic Press, New York, 1986, p95.
2. Dörnyei, G.; Szántay, C. Heterocycles, 1994, 39, 449 and references cited therein.
3. (a) Vizi, E. S.; Toth, L; Somogyi, G. T.; Szabo, L.; Harsing, Jr., L. G.; Szantay, C. J . Med. Chem., 1987, 30, 1355.
4. (b) Zimanyi, I.; Lajtha, A.; Vozi, E. S.; Wang, E.; Reith, M. E. A. Neurophamacology, 1988, 27, 1205.
5. (a) Yamaguchi, R.; Moriyasu, M.; Yoshioka, M.; M. Kawanisi J. Org. Chem. 1988, 53, 3507.
6. (b) Yamaguchi, R.; Mochizuki, K.; Kozima, S.; Takaya, H. J. Chem. Soc., Chem. Commun. 1993, 981.
7. (c) Yamaguchi, R.; Mochizuki, K.; Kozima, S.; Takaya, H. Chem. Lett. 1994, 1908.
8. (d) Hatano, B.; Haraguchi, Y.; Kozima, S.; Yamaguchi, R. Chem. Lett. 1995, 1003.
9. Yamaguchi, R.; Otsuji, A.; Utimoto, K. J. Am. Chem. Soc. 1988, 110, 2186.
10. Yamaguchi, R.; Hamasaki, T.; Sasaki, T.; Ohta, T.; Utimoto, K.; Kozima, S.; Takaya, H. J. Org. Chem. 1993, 58, 1136.
11. Schrecker, A. W.; Hartwell, J. L. J. Am. Chem. Soc. 1957, 79, 3827.
12. O'Reilly, N. J.; Derwin, W. S.; Lin, H. C. Synthesis 1990, 550.
13. 1H NMR differential NOE experiments showed that there is 4.5% NOE between the methylene protons of the siloxymethyl group and H1.
14. 1H NMR differential NOE experiments showed that there is 3.7% NOE between the methylene protons of the siloxymethyl group and H1.