A reinvestigation of the reported synthesis of the spironzyl isoquinoline alkaloid, iso-ochotensine

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4195-4198

  Meyers, A I ^a   Akahane, Atsushi ^a   Struzka, Vladimir ^a   Warmus, Joseph S ^a   Gonzalez, Michael ^a   Milot, Guy ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE ALKALOID;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030972837     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00869-1     Document Type: Article

References (23)

1. Highsmith, T. K.; Meyers, A. I. Advances in Heterocyclic Natural Product Synthesis; JAI: 1990; Vol. 1, pp 95-135. For details on the procedure, see, Meyers, A. I.; Bos, M.; Dickman, D. A. Org. Syn. Coll. Vol. VIII, p. 573, J. Wiley, 1993.
2. Highsmith, T. K.; Meyers, A. I. Advances in Heterocyclic Natural Product Synthesis; JAI: 1990; Vol. 1, pp 95-135. For details on the procedure, see, Meyers, A. I.; Bos, M.; Dickman, D. A. Org. Syn. Coll. Vol. VIII, p. 573, J. Wiley, 1993.
3. (a) Manske, R. H. F. The Alkaloids 1971 13, p. 166, Academic.
4. (b) Manske, R. H. F. Can J. Res. 1936 14B, 354.
5. (c) Manske, R. H. F. Can. J. Res. 1940 18B, 75.
6. (d) Ito, S. Natural Products Chemistry; Nakanishi, K.; Goto, T.; Ito, S.; Natori, S.; Nozoe, S., Ed.; Academic: New York, 1975; Vol. 2, pp 310-313.
7. (e) Saunders, J. K.; Bell, R. A.; Chen, C.-Y.; MacLean, D. B.; Manske, R. H. F. Can. J. Chem. 1968, 46, 2873.
8. (f) ibid. 1968, 40, 2876.
9. (g) McLean, S.; Lin, M. S. Tetrahedron Lett. 1964, 3819.
10. (h) The X-ray structure of ochotensine has been reported: McLean, S.; Lin, M. S.; MacDonald, A. C.; Trottel, J. Tetrahedron Lett. 1966, 185.
11. Meyers, A. I.; Gonzalez, M. A; Struzka, V.; Akahane, A.; Guiles, J.; Warmus, J. S. Tetrahedron Lett. 1991, 32, 5501.
12. McLean, S.; Lin, M. S.; Whelan, J. Tetrahedron Lett. 1968, 2425.
13. Irie, H.; Kishimoto, T.; Uyeo, S. J. Chem. Soc. (C) 1968, 3051.
14. (a) Kametani, T.; Takano, S.; Hibino, S.; Terui, T. J. Heterocyclic Chem. 1969, 6, 49.
15. (b) Kametani, T.; Takano, S.; Hibino, S. J. Pharm. Soc. Japan 1968, 88, 1123.
16. Shamma, M.; Jones, C. D. J. Am. Chem. Soc. 1969, 91, 4009.
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21. 3, δ) 1.40 (t, 3), 2.74 (dd, 1), 3.06 (m, 1), 3.17 (d, 1), 3.31 (dt, 1), 3.41 (d, 1), 3.94 (s, 3), 4.26 (m, 1), 4.33 (q, 2), 5.96 (s, 2), 6.59 (s, 1), 6.60 (d, 1) 6.75 (d, 1), 6.97 (s, 1), 7.38 (s, 1).
22. Shamma, M.; Jones, C. D. J. Org. Chem. 1970, 35, 3119.
23. Attempts to secure samples or spectra from the late Professor Kametani's laboratory did not meet with any success.