Indol-2-one intermediates: Mechanistic evidence and synthetic utility. Total syntheses of (±)-flustramines A and C

Organic Letters

Volumn 7, Issue 4, 2005, Pages 677-680

  Fuchs, James R ^a   Funk, Raymond L ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CESIUM; FLUSTRAMINE A; FLUSTRAMINE C; INDOLE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DIELS ALDER REACTION; MICHAEL ADDITION; MOLECULAR INTERACTION; PRENYLATION; SYNTHESIS;

ALKALOIDS; HETEROCYCLIC COMPOUNDS, 3-RING; INDICATORS AND REAGENTS; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 14844363196     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047532v     Document Type: Article

References (23)

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2. For the generation and Diels-Alder cycloaddition of the related 2-azacyclopenta-2,4-dien-1-one with polymer-supported acetylene-dicarboxylate, see: (a) Gavina, F.; Costero, A. M.; Andreu, M. R.; Carda, M.; Luis, S. V. J. Am. Chem. Soc. 1988, 110, 4017. (b) Yokotsuji, D. L. S.; Dailey, W. P.; Kende, A. S.; Birzan, L.; Liu, K. J. Phys. Chem. 1995, 99, 15870.
3. For the generation and Diels-Alder cycloaddition of the related 2-azacyclopenta-2,4-dien-1-one with polymer-supported acetylene-dicarboxylate, see: (a) Gavina, F.; Costero, A. M.; Andreu, M. R.; Carda, M.; Luis, S. V. J. Am. Chem. Soc. 1988, 110, 4017. (b) Yokotsuji, D. L. S.; Dailey, W. P.; Kende, A. S.; Birzan, L.; Liu, K. J. Phys. Chem. 1995, 99, 15870.
4. Alternative pathways for the formation of indolenine 4 were also envisaged, including direct displacement and transfer alkylation.
5. (a) Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 2431.
6. For further examples of reactions that may occur via generation of indol-2-one intermediates, see: (b) Labroo, R. B.; Labroo, V. M.; King, M. M.; Cohen, L. A. J. Org. Chem. 1991, 56, 3637. (c) Rajeswaran, W. G.; Labroo, R. B.; Cohen, L. A.; King, M. M. J. Org. Chem. 1999, 64, 1369. (d) Kobayashi, M.; Aoki, S.; Gato, K.; Matsunami, K.; Kurosu, M.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2449. For an example of an intramolecular displacement of a tertiary mesylate with inversion of stereochemistry, see: Monde, K.; Taniguchi, T.; Miura, N.; Nishimura, S.-I.; Harada, N.; Dukor, R. K.; Nafie, L. A. Tetrahedron Lett. 2003, 44, 6017.
7. For further examples of reactions that may occur via generation of indol-2-one intermediates, see: (b) Labroo, R. B.; Labroo, V. M.; King, M. M.; Cohen, L. A. J. Org. Chem. 1991, 56, 3637. (c) Rajeswaran, W. G.; Labroo, R. B.; Cohen, L. A.; King, M. M. J. Org. Chem. 1999, 64, 1369. (d) Kobayashi, M.; Aoki, S.; Gato, K.; Matsunami, K.; Kurosu, M.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2449. For an example of an intramolecular displacement of a tertiary mesylate with inversion of stereochemistry, see: Monde, K.; Taniguchi, T.; Miura, N.; Nishimura, S.-I.; Harada, N.; Dukor, R. K.; Nafie, L. A. Tetrahedron Lett. 2003, 44, 6017.
8. For further examples of reactions that may occur via generation of indol-2-one intermediates, see: (b) Labroo, R. B.; Labroo, V. M.; King, M. M.; Cohen, L. A. J. Org. Chem. 1991, 56, 3637. (c) Rajeswaran, W. G.; Labroo, R. B.; Cohen, L. A.; King, M. M. J. Org. Chem. 1999, 64, 1369. (d) Kobayashi, M.; Aoki, S.; Gato, K.; Matsunami, K.; Kurosu, M.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2449. For an example of an intramolecular displacement of a tertiary mesylate with inversion of stereochemistry, see: Monde, K.; Taniguchi, T.; Miura, N.; Nishimura, S.-I.; Harada, N.; Dukor, R. K.; Nafie, L. A. Tetrahedron Lett. 2003, 44, 6017.
9. For further examples of reactions that may occur via generation of indol-2-one intermediates, see: (b) Labroo, R. B.; Labroo, V. M.; King, M. M.; Cohen, L. A. J. Org. Chem. 1991, 56, 3637. (c) Rajeswaran, W. G.; Labroo, R. B.; Cohen, L. A.; King, M. M. J. Org. Chem. 1999, 64, 1369. (d) Kobayashi, M.; Aoki, S.; Gato, K.; Matsunami, K.; Kurosu, M.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2449. For an example of an intramolecular displacement of a tertiary mesylate with inversion of stereochemistry, see: Monde, K.; Taniguchi, T.; Miura, N.; Nishimura, S.-I.; Harada, N.; Dukor, R. K.; Nafie, L. A. Tetrahedron Lett. 2003, 44, 6017.
10. These conditions had been previously employed for the generation of N-acyl and N-sulfonyl-aza-ortho-xylylenes. Steinhagen, H.; Corey, E. J. Angew. Chem., Int. Ed. 1999, 38, 1928.
11. For a reference scale of π-nucleophilicity, see: (a) Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66. (b) Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500.
12. For a reference scale of π-nucleophilicity, see: (a) Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66. (b) Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500.
13. Previous studies have suggested that the seven-membered ring closure is preferred geometrically in internal electrophilic aromatic substitution reactions. Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3349.
14. Kende, A. S.; Hodges, J. C. Synth. Commun. 1982, 12, 1.
15. Kamatani, A.; Overman, L. E. J. Org. Chem. 1999, 64, 8743.
16. For the isolation from Flustra foliacea (L.), see: (a) Carle, J. S.; Christophersen, C. J. Org. Chem. 1980, 45, 1586. For the previous total synthesis, see: (b) Morales-Rios, M. S.; Suarez-Castillo, O. R.; Trujillo-Serrato, J. J.; Joseph-Nathan, P. J. Org. Chem. 2001, 66, 1186.
17. For the isolation from Flustra foliacea (L.), see: (a) Carle, J. S.; Christophersen, C. J. Org. Chem. 1980, 45, 1586. For the previous total synthesis, see: (b) Morales-Rios, M. S.; Suarez-Castillo, O. R.; Trujillo-Serrato, J. J.; Joseph-Nathan, P. J. Org. Chem. 2001, 66, 1186.
18. For the isolation from Flustra foliacea (L.), see: (a) Carle, J. S.; Christophersen, C. J. Org. Chem. 1981, 46, 3440. For the previous total synthesis, see: (b) Kawasaki, T.; Terashima, R.; Sakaguchi, K.; Sekiguchi, H.; Sakamoto, M. Tetrahedron Lett. 1996, 37, 7525.
19. For the isolation from Flustra foliacea (L.), see: (a) Carle, J. S.; Christophersen, C. J. Org. Chem. 1981, 46, 3440. For the previous total synthesis, see: (b) Kawasaki, T.; Terashima, R.; Sakaguchi, K.; Sekiguchi, H.; Sakamoto, M. Tetrahedron Lett. 1996, 37, 7525.
20. For the total synthesis of related pyrrolidinoindoline alkaloids via reverse prenylation of putative N-acyl-aza-ortho-xylylenium ions, see: (a) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (b) Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11953. (c) Schiavi, B. M.; Richard, D. J.; Joullie, M. M. J. Org. Chem. 2002, 67, 620.
21. For the total synthesis of related pyrrolidinoindoline alkaloids via reverse prenylation of putative N-acyl-aza-ortho-xylylenium ions, see: (a) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (b) Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11953. (c) Schiavi, B. M.; Richard, D. J.; Joullie, M. M. J. Org. Chem. 2002, 67, 620.
22. For the total synthesis of related pyrrolidinoindoline alkaloids via reverse prenylation of putative N-acyl-aza-ortho-xylylenium ions, see: (a) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (b) Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11953. (c) Schiavi, B. M.; Richard, D. J.; Joullie, M. M. J. Org. Chem. 2002, 67, 620.
23. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.