New pyridone approach: Total synthesis of mappicine ketone (nothapodytine B)

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5212-5215

  Mekouar, Khalid ^a   Génisson, Yves ^a,b   Leue, Stefanie ^a   Greene, Andrew E ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

^b UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANTIVIRUS AGENT; DIPYRONE; ESTER; KETONE DERIVATIVE; MAPPICINE KETONE; NOTHAPODYTINE B; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DECARBOXYLATION; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

ANTIVIRAL AGENTS; HERPESVIRIDAE; INDOLIZINES; QUINOLINES; SPECTRUM ANALYSIS;

EID: 0342955694     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0003448     Document Type: Article

References (32)

1. Wu, T.-S.; Chan, Y.-Y.; Leu, Y.-L.; Chern, C.-Y.; Chen, C.-F. Photochemistry 1996, 42, 907-908. The corresponding alcohol, mappicine, has been found in Mapia foetida Miers (now Nothapodytes foetida). See: Govindachari, T. R.; Ravindranath, K. R.; Viswanathan, N. J. Chem. Soc., Perkin Trans. 1 1974, 1215-1217. Reference 3c.
2. Wu, T.-S.; Chan, Y.-Y.; Leu, Y.-L.; Chern, C.-Y.; Chen, C.-F. Photochemistry 1996, 42, 907-908. The corresponding alcohol, mappicine, has been found in Mapia foetida Miers (now Nothapodytes foetida). See: Govindachari, T. R.; Ravindranath, K. R.; Viswanathan, N. J. Chem. Soc., Perkin Trans. 1 1974, 1215-1217. Reference 3c.
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8. For total syntheses of mappicine ketone, see: (a) Kametani, T.; Takeda, H.; Nemoto, H.; Fukumoto, K. Heterocycles 1975, 3, 167-170. Kametani, T.; Takeda, H.; Nemoto, H.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1975, 1825-1828.
9. For total syntheses of mappicine ketone, see: (a) Kametani, T.; Takeda, H.; Nemoto, H.; Fukumoto, K. Heterocycles 1975, 3, 167-170. Kametani, T.; Takeda, H.; Nemoto, H.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1975, 1825-1828.
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14. Meth-Cohn, O.; Narine, B.; Tarnowski, B. J. Chem. Soc., Perkin Trans. 1 1981, 1520-1530. This aldehyde is also available from the Aldrich Chemical Co.
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17. (b) The alcohol precursor was obtained as previously described: Srivastava, R. P.; Seth, M.; Bhaduri, A. P.; Bhatnagar, S.; Guru, P. Y. Indian J. Chem., Sect. B 1989, 28, 562-573. Narasimhan, N. S.; Sunder, N. M.; Ammanamanchi, R.; Bonde, B. D. J. Am. Chem. Soc. 1990, 112, 4431-4435. Ciufolini, M. A.; Roschangar, F. Tetrahedron 1997, 53, 11049-11060.
18. (b) The alcohol precursor was obtained as previously described: Srivastava, R. P.; Seth, M.; Bhaduri, A. P.; Bhatnagar, S.; Guru, P. Y. Indian J. Chem., Sect. B 1989, 28, 562-573. Narasimhan, N. S.; Sunder, N. M.; Ammanamanchi, R.; Bonde, B. D. J. Am. Chem. Soc. 1990, 112, 4431-4435. Ciufolini, M. A.; Roschangar, F. Tetrahedron 1997, 53, 11049-11060.
19. (b) The alcohol precursor was obtained as previously described: Srivastava, R. P.; Seth, M.; Bhaduri, A. P.; Bhatnagar, S.; Guru, P. Y. Indian J. Chem., Sect. B 1989, 28, 562-573. Narasimhan, N. S.; Sunder, N. M.; Ammanamanchi, R.; Bonde, B. D. J. Am. Chem. Soc. 1990, 112, 4431-4435. Ciufolini, M. A.; Roschangar, F. Tetrahedron 1997, 53, 11049-11060.
20. Gómez, A. M.; López, J. C.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1994, 1689-1695. See also: Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867. For a review of the Stille reaction, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
21. Gómez, A. M.; López, J. C.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1994, 1689-1695. See also: Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867. For a review of the Stille reaction, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
22. Gómez, A. M.; López, J. C.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1994, 1689-1695. See also: Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867. For a review of the Stille reaction, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
23. See: Ihara, M.; Kirihara, T.; Kawaguchi, A.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Perkin Trans. 1 1987, 1719-1726. A Diels-Alder reaction of the silyl imino ether is also possible.
24. In a closely related model system, it was found that a p-tolylsulfonyl group could not be used in place of the methoxycarbonyl in this cyclization.
25. Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617.
26. For the efficient preparation of the corresponding ester, see: Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254-2256. The acid reacted also with azide 4b in the presence of triphenylphosphine to provide more directly the same amide, but in lower yield (60%) than achieved in the two-step conversion (82%). For this synthetic method, see: Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844.
27. For the efficient preparation of the corresponding ester, see: Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254-2256. The acid reacted also with azide 4b in the presence of triphenylphosphine to provide more directly the same amide, but in lower yield (60%) than achieved in the two-step conversion (82%). For this synthetic method, see: Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844.
28. These conditions have previously been used to effect the conversion of a terpenoid enol lactone into the corresponding α-pyrone. See: Rosenthal, D.; Grabowich, P.; Sabo, E. F.; Fried, J. J. Am. Chem. Soc. 1963, 85, 3971-3979.
29. That the presence of the keto function was not critical in this transformation was demonstrated by the transformation of i to ii. (For comparison, DDQ provided ii in only 20% yield.) Formula represented
30. The mixture of minor stereoisomers formed in the cyclization of ester 10b was also converted, in the same manner and with an identical overall yield, into mappicine ketone.
31. Mekouar, K.; Génisson, Y.; Leue, S.; Greene, A. E. Fr Appl 99/06757, 28 May 1999. See also: Toyota, M.; Komori, C.; Ihara, M. Heterocycles 2000, 52, 591-593.
32. Mekouar, K.; Génisson, Y.; Leue, S.; Greene, A. E. Fr Appl 99/06757, 28 May 1999. See also: Toyota, M.; Komori, C.; Ihara, M. Heterocycles 2000, 52, 591-593.