A new, more efficient, and effective process for the synthesis of a key pentacyclic intermediate for production of ecteinascidin and phthalascidin antitumor agents

Organic Letters

Volumn 2, Issue 7, 2000, Pages 993-996

  Martinez, Eduardo J ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ANTINEOPLASTIC AGENT; ISOQUINOLINE DERIVATIVE; PHTHALASCIDIN; PHTHALIMIDE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; TRABECTEDIN;

ARTICLE; CATALYSIS; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CATALYSIS; DIOXOLES; ISOQUINOLINES; PHTHALIMIDES; TETRAHYDROISOQUINOLINES;

EID: 0034611483     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0056729     Document Type: Article

References (19)

1. The pioneering research in this area is due to Prof. Kenneth L. Rinehart and his group. See: (a) Rinehart, K. L.; Shield, L. S. In Topics in Pharmaceutical Sciences; Breimer, D. D., Crommelin, D. J. A., Midha, K. K., Ed.; Amsterdam Medical Press: Noordwijk, The Netherlands, 1989; p 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. U.S.A. 1992, 89, 11456.
7. (a) Business Week September 13, 1999, 22.
8. (b) Science 1994, 266, 1324.
9. Corey, E. J.; Gin, D. Y.; Kania, R. J. Am. Chem. Soc. 1996, 118, 9202.
10. Martinez, E. J.; Owa, T.; Schreiber, S. L.; Corey, E. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 3496.
11. See: Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828 for a different approach to the synthesis of structures such as 5.
12. For carboxylic acid-amine coupling methodology using CIP, see: (a) Akaji, K.; Kuriyama, N.; Kimura, T.; Fujiwara, Y.; Kiso, Y. Tetrahedron Lett. 1992, 33, 3177.
13. (b) Akaji, K.; Kuriyama, N.; Kiso, Y. Tetrahedron Lett. 1994, 35, 3315.
14. (c) Akaji, K.; Kuriyama, N.; Kiso, Y. J. Org. Chem. 1996, 61, 3350.
15. 4 in ether solvent at 0 °C and stirring at 0 °C for 2 h just before use; see: Brown, H. C.; Tsukamoto, A. J. Am. Chem. Soc. 1964, 86, 1089.
16. For general reviews on the reduction of lactones, see: (a) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567.
17. (b) Cha, J. S. Org. Prep. Proc. Int. 1989, 21(4), 451.
18. (c) Seyden-Penne, J. Reduction by the Alumino-and Borohydrides in Organic Synthesis, 2nd ed.; Wiley-VCH: New York, 1997; Section 3.2.5.
19. For general references on amide reduction by hydride reagents, see ref 7 and also the following: Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361.