A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)

Angewandte Chemie - International Edition

Volumn 42, Issue 41, 2003, Pages 5059-5061

  Raolji, Gajendra B ^a   Garçon, Stéphanie ^a   Greene, Andrew E ^a   Kanazawa, Alice ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Cross coupling; Cycloaddition; Isomerization; Rearrangement; Total synthesis

Indexed keywords

CHEMOTHERAPY; DERIVATIVES; KETONES; SYNTHESIS (CHEMICAL);

BIOLOGICAL TESTING;

NITROGEN COMPOUNDS;

ANTIVIRUS AGENT; CAMPTOTHECIN; KETONE DERIVATIVE; MAPPICINE; NOTHAPODYTINE A; NOTHAPODYTINE B; OXOINDOLIZINOQUINOLINE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CLAISEN REARRANGEMENT; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICINAL PLANT; NONHUMAN; NOTHAPODYTES FOETIDA; REACTION ANALYSIS; STRUCTURE ANALYSIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; INDOLIZINES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; QUINOLINES;

EID: 0242323509     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352094     Document Type: Article

References (30)

1. T.-S. Wu, Y.-Y. Chan, Y.-L. Leu, C.-Y. Chern, C.-F. Chen, Phytochemistry 1996, 42, 907-908.
2. T. R. Govindachari, K. R. Ravindranath, N. Viswanathan, J. Chem. Soc. Perkin Trans. 1 1974, 1215-1217.
3. Reviews on camptothecin and derivatives: a) Camptothecins: New Anticancer Agents (Eds.: M. Potmesil, H. Pinedo), CRC, Boca Raton, 1995;
4. b) S. Sawada, T. Yokokura, T. Miyasaka, Curr. Pharm. Des. 1995, 1, 113-132;
5. c) M. Torck, M. Pinkas, J. Pharm. Belg. 1996, 51, 200-207;
6. d) C. R. Hutchinson, Tetrahedron 1981, 37, 1047-1065.
7. G. Stork, A. G. Schultz, J. Am. Chem. Soc. 1971, 93, 4074-4075.
8. Review on Friedländer quinoline synthesis: C.-C. Cheng, S. J. Yan, Org. React. 1982, 28, 37-201.
9. a) Reviews on the Claisen rearrangement: S. J. Rhoads, N. R. Raulins, Org. React. 1975, 22, 1-252; S. Blechert, Synthesis 1989, 71-82;
10. a) Reviews on the Claisen rearrangement: S. J. Rhoads, N. R. Raulins, Org. React. 1975, 22, 1-252; S. Blechert, Synthesis 1989, 71-82;
11. b) Review on Stille coupling: V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1-652;
12. c) Reviews on Suzuki coupling: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
13. c) Reviews on Suzuki coupling: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
14. c) Reviews on Suzuki coupling: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
15. Reviews on carbonyl ylide cycloaddition: a) M. C. McMills, D. Wright in The Chemistry of Heterocyclic Compounds: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (Eds.: A. Padwa, W. H. Pearson), Wiley, New York, 2002, pp. 253-314;
16. b) G. Mehta, S. Muthusamy, Tetrahedron 2002, 58, 9477-9504.
17. a) J. M. D. Fortunak, A. R. Mastrocola, M. Mellinger, J. L. Wood, Tetrahedron Lett. 1994, 35, 5763-5764;
18. b) B. Das, P. Madhusudhan, A. Kashinatham, Bioorg. Med. Chem. Lett. 1998, 8, 1403-1406;
19. c) See also W. D. Kingsbury, Tetrahedron Lett. 1988, 29, 6847-6850; B. Das, P. Madhusudhan, A. Kashinatham, Tetrahedron Lett. 1998, 39, 431-432.
20. c) See also W. D. Kingsbury, Tetrahedron Lett. 1988, 29, 6847-6850; B. Das, P. Madhusudhan, A. Kashinatham, Tetrahedron Lett. 1998, 39, 431-432.
21. a) I. Pendrak, S. Barney, R. Wittrock, D. M. Lambert, W. D. Kingsbury, J. Org. Chem. 1994, 59. 2623-2625;
22. b) I. Pendrak, R. Wittrock, W. D. Kingsbury, J. Org. Chem. 1995, 60, 2912-2915.
23. Previous syntheses of mappicine ketone: L. Carles, K. Narkunan, S. Penlou, L. Rousset, D. Bouchu, M. A. Ciufolini, J. Org. Chem. 2002, 67, 4304-4308, and references therein.
24. A. Padwa, S. M. Sheehan, C. S. Straub, J. Org. Chem. 1999, 64, 8648-8659.
25. Two other examples: a) B. B. Jarvis, C. B. Anderson, J. Heterocycl. Chem. 1983, 20, 471-473;
26. b) K. C. Majumdar, A. K. Kundu, P. Chatterjee, J. Chem. Res. Synop. 1995, 386-387.
27. a) J. Andrieux, D. H. R. Barton, H. Patin, J. Chem. Soc. Perkin Trans. 1 1977, 359-363;
28. b) P. A. Grieco, N. Marinovic, Tetrahedron Lett. 1978, 2545-2548.
29. a) E. J. Corey, H. E. Ensley, J. Am. Chem. Soc. 1975, 97, 6908-6909;
30. b) W. Shen, C. A. Coburn, W. G. Bornmann, S. J. Danishefsky, J. Org. Chem. 1993, 58, 611-617.