Studies directed to the total synthesis of ET 743 and analogues thereof: An expeditious route to the ABFGH subunit

Organic Letters

Volumn 4, Issue 1, 2002, Pages 43-45

  Zhou, Bishan ^a   Guo, Jinsong ^a   Danishefsky, Samuel J ^a,b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ALKYLATING AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ISOQUINOLINE DERIVATIVE; LACTONE; SPIRO COMPOUND; TETRAHYDROISOQUINOLINE DERIVATIVE; TRABECTEDIN;

ANIMAL; ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; UROCHORDATA;

ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; DIOXOLES; INDICATORS AND REAGENTS; ISOQUINOLINES; LACTONES; MOLECULAR CONFORMATION; SPIRO COMPOUNDS; STEREOISOMERISM; TETRAHYDROISOQUINOLINES; UROCHORDATA;

EID: 0037050417     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016844k     Document Type: Article

References (24)

1. (a) 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.
2. (b) Sakai, R.; Rinehart, K. L.; Guan, Y.; Wang, A. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11456.
3. Saframycins: (a) Moore, B. M.; Miranda, N. F. J. Nat. Prod. 1995, 58. 1616.
4. (b) Takahashi, F.; Kubo, A. J. Antibiot. 1977 30, 1015.
5. (c) Quinocarcin: Tomita, F.; Takahashi, K.; Shimuzu, K. J. Antibiot. 1983, 36, 468.
6. (d) Renieramycin: Zmijewski, M. J.; Goebel, M. J. Antibiot. 1982, 35, 524.
7. For the previous synthetic approaches on saframycins, Et743, and their related natural products, see: (e) Saito, N.; Tashiro, K.; Maru, Y.; Yamaguchi, K.; Kubo, A. J. Chem. Soc., Perkin Trans. 1 1997, 53.
8. (f) Saito, N.; Tachi, M.; Seki, R.; Kamayaci, H.; Kubo, A. Chem. Pharm. Bull. 2000, 48, 1549.
9. (g) Saito, N.; Kamayachi, H.; Tachi, M.; Kubo, A. Heterocycles 1999, 51, 9.
10. (h) Endo, A.; Kann, T.; Fukuyama, T. Synlett 1999, 1103.
11. (i) Herberich, B.; Vazquez, A.; Kinugawa, M.; Jin. W.; Williams, R. M. Tetrahedron Lett. 2001, 42, 543.
12. (j) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828.
13. (a) Sakai, R.; Jares-Erijiman, E. A.; Manzanares, I.; Silva Elipe, M. V.; Rinehart, K. L. J. Am. Chem. Soc. 1996, 118, 9017.
14. (b) Zewail-Foote, M.; Hurley, L. H. J. Med. Chem. 1999, 42, 2493.
15. (c) Borman, S. Chem. Eng. News 2001, 79, 41.
16. Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202.
17. Cuevas, C.; Perez, M.; Martin, M. J.; Chicharro, J. L.; Fernandez-Rivas, C.; Flores, M.; Francesch, A.; Gallego, P.; Zarzuelo, M.; Calle, F.; Garcia, J.; Polanco, C.; Rodriguez, I.; Manzanares, I. Org. Lett. 2000, 16, 2545.
18. Zhou, B.; Guo J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. Since this work appeared, we now recognize that in this cyclization, the stereochemistry at C1 controls the sense of the Mannich closure at C3. The reaction is such that the hydrogens at C1 and C3 will emerge trans. The origin of this effect, and its consequences for reaching Et743 by chemical synthesis has been discussed extensively in ref 10 and will be described shortly.
19. (a) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039.
20. The experimental procedures for the conversion of 20 → 21 are provided as Supporting Information. For recent applications of the Pomeranz-Fritsch reaction, see: (b) Ponzo, V. L.; Kaufman, T. S. J. Chem. Soc., Perkin Trans. 1 1997, 3131.
21. (c) Scott, J. D.; Williams, R. M. Angew. Chem., Int. Ed. 2001, 40, 1463.
22. Sharpless, K. B.; Hartung, J.; Jeong, K.; Kwong, H.; Morikawa, K.; Wang, Z.; Xu, D.; Zhang, X. J. Org. Chem. 1992, 57, 2768.
23. Danishefsky, S. J.; Doehner, R. Tetrahedron Lett. 1977, 35, 3031.
24. Zhou, B. Ph.D. Thesis, Columbia University, 2001.