A convergent enantioselective synthesis of the tetrahydroisoquinoline unit in the spiro ring of ecteinascidin 743

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7163-7166

  Corey, E J ^a   Gin, David Y ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; TETRAHYDROISOQUINOLINE DERIVATIVE; TRABECTEDIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0030607146     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01622-X     Document Type: Article

References (16)

1. 1 (a) Rinehart, K. L.; Shield, L. S. in Topics in Pharmaceutical Sciences, eds. Breimer, D. D.; Crommelin, D. J. A.; Midha, K. K. (Amsterdam Medical Press, Noordwijk, The Netherlands), 1989, pp. 613.
2. (b) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Keifer, P. A.; Wilson, G. R.; Perun, T. J., Jr.; Sakai, R.; Thompson, A. G.; Stroh, J. G.; Shield, L. S.; Seigler, D. S.; Li, L. H.; Martin, D. G.; Grimmelikhuijzen, C. J. P.; Gäde, G. J. Nat. Prod. 1990, 53, 771.
3. (c) Rinehart, K. L.; Sakai, R; Holt, T. G.; Fregeau, N. L.; Perun, T. J., Jr.; Seigler, D. S.; Wilson, G. R.; Shield, L. S. Pure Appl. Chem. 1990, 62, 1277.
4. (d) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Keifer, P. A.; Sun, F.; Li, L. H.; Martin, D. G. J. Org. Chem. 1990, 55, 4512.
5. (e) Wright, A. E.; Forleo, D. A.; Gunawardana, G. P.; Gunasekera, S. P.; Koehn, F. E.; McConnell, O. J. J. Org. Chem. 1990, 55, 4508.
6. (f) Sakai, R.; Rinehart, K. L.; Guan, Y.; Wang, H.-J. Proc. Natl. Acad. Sci. USA 1992, 89, 11456.
7. 2. For previous work on the synthesis of the saframycins see: (a) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957.
8. (b) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712.
9. (c) Saito, N.; Yamauchi, R.; Nishioka, H.; Ida, S.; Kubo, A. J. Org. Chem. 1989, 54, 5391.
10. 23 for 12 = -15.5 and for 13 = +15.5 (c=3, EtOH).
11. 4. The method of preparation of 9 was analogous to that described for ethyl 3-mercaptopyruvate: Taylor, E. C.; Reiter, L. A. J. Am. Chem. Soc. 1989, 111, 285.
12. 4 reduction product of 12: (equation presented)
13. 6. Crystal structure solved by Dr. Axel Fischer.
14. +) 510.2678, found 510.2700.
15. 8. Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. submitted.
16. 9. This research was assisted financially by the National Institutes of Health and a Canadian NSERC fellowship to DYG.