Brønsted acid-catalyzed highly stereoselective arene-ynamide cyclizations. A novel keteniminium Pictet-Spengler cyclization in total syntheses of (±)-desbromoarborescidines A and C

Organic Letters

Volumn 7, Issue 6, 2005, Pages 1047-1050

  Zhang, Yanshi ^a   Hsung, Richard P ^a   Zhang, Xuejun ^a   Huang, Jian ^a   Slafer, Brian W ^a   Davis, Allison ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKALOID DERIVATIVE; BROMINE DERIVATIVE; BRONSTED ACID; DESBROMOARBORESCIDINE A; DESBROMOARBORESCIDINE C; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; PICTET SPENGLER CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

CATALYSIS; CYCLIZATION; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 18244388692     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0473391     Document Type: Article

References (63)

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3. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
4. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
5. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
6. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
7. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
8. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
9. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
10. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
11. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
12. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
13. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
14. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
15. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
16. For recent efforts in synthesis and applications of ynamides, see: (a) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084. (b) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511. (c) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783. (d) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377. (e) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6. 727. (f) Klein, M.; König, B. Tetrahedron 2004, 60, 1087. (g) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095. (h) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392. (i) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67. (j) Witulski, B.; Lumtscher, J.; Bergsträsser, U. Synlett 2003, 708. (k) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391. (l) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281. (m) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803. (n) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
17. 2-catalyzed en-ynamide cyclization, see: Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509.
18. For our recent contributions, see: (a) Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209. (b) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (c) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (d) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (e) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (f) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
19. For our recent contributions, see: (a) Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209. (b) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (c) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (d) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (e) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (f) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
20. For our recent contributions, see: (a) Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209. (b) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (c) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (d) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (e) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (f) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
21. For our recent contributions, see: (a) Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209. (b) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (c) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (d) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (e) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (f) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
22. For our recent contributions, see: (a) Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209. (b) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (c) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (d) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (e) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (f) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
23. For our recent contributions, see: (a) Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209. (b) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353. (c) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A. Tracey, M. R. Org. Lett. 2003, 5, 2663. (d) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547. (e) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417. (f) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
24. For copper-catalyzed amidations of alkynyl bromides, see: (a) Zhang, Y.; Hsung R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151. (b) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
25. For copper-catalyzed amidations of alkynyl bromides, see: (a) Zhang, Y.; Hsung R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151. (b) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
26. Also see: (a) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011. (b) Reference 2e.
27. Also see: (a) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011. (b) Reference 2e.
28. For a review, see: Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
29. For other reviews, see: (a) Méndez, M.; Mamane, V.; Fürstner, A. ChemTracts 2003, 16, 397. (b) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215.
30. For other reviews, see: (a) Méndez, M.; Mamane, V.; Fürstner, A. ChemTracts 2003, 16, 397. (b) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215.
31. For recent examples of enyne cyclizations, see: (a) Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408. (b) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055. (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414. (e) Fürstner, A.; Mamune, V. J. Org. Chem. 2002, 67, 6264.
32. For recent examples of enyne cyclizations, see: (a) Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408. (b) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055. (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414. (e) Fürstner, A.; Mamune, V. J. Org. Chem. 2002, 67, 6264.
33. For recent examples of enyne cyclizations, see: (a) Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408. (b) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055. (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414. (e) Fürstner, A.; Mamune, V. J. Org. Chem. 2002, 67, 6264.
34. For recent examples of enyne cyclizations, see: (a) Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408. (b) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055. (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414. (e) Fürstner, A.; Mamune, V. J. Org. Chem. 2002, 67, 6264.
35. For recent examples of enyne cyclizations, see: (a) Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408. (b) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055. (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414. (e) Fürstner, A.; Mamune, V. J. Org. Chem. 2002, 67, 6264.
36. For some examples of Brønsted acid catalysis, see: (a) Williams, A. L.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 1612. (b) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204. (c) Cossy, J.; Lutz, F.; Alauze, V.; Meyer, C. Synlett 2002, 45. (d) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851.
37. For some examples of Brønsted acid catalysis, see: (a) Williams, A. L.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 1612. (b) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204. (c) Cossy, J.; Lutz, F.; Alauze, V.; Meyer, C. Synlett 2002, 45. (d) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851.
38. For some examples of Brønsted acid catalysis, see: (a) Williams, A. L.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 1612. (b) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204. (c) Cossy, J.; Lutz, F.; Alauze, V.; Meyer, C. Synlett 2002, 45. (d) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851.
39. For some examples of Brønsted acid catalysis, see: (a) Williams, A. L.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 1612. (b) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204. (c) Cossy, J.; Lutz, F.; Alauze, V.; Meyer, C. Synlett 2002, 45. (d) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851.
40. (a) For an excellent review, see: Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
41. (b) For an excellent review on additions to N-acyl or N-sulfonyl iminium ions, see: Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
42. For some elegant examples of Pictet-Spengler cyclizations, see: (a) Yu, J.; Wang, T.; Liu, X.; Deschamps, J.; Flippen-Anderson, J.; Liao, X.; Cook, J. M. J. Org. Chem. 2003, 68, 7565-7581. (b) Yu, J.; Wearing, X.; Cook, J. M. Tetrahedron Lett. 2003, 44, 543.
43. For some elegant examples of Pictet-Spengler cyclizations, see: (a) Yu, J.; Wang, T.; Liu, X.; Deschamps, J.; Flippen-Anderson, J.; Liao, X.; Cook, J. M. J. Org. Chem. 2003, 68, 7565-7581. (b) Yu, J.; Wearing, X.; Cook, J. M. Tetrahedron Lett. 2003, 44, 543.
44. For a recent example on catalytic asymmetric Pictet-Spengler cyclization, see: Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
45. For isolation of 10-desbromoarborescidine A, see: Johns, S. R.; Lamberton, J. A.; Occolowitz, J. L. Aust. J. Chem. 1966, 19, 1951.
46. For total syntheses of arborescidine A, see: (a) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (b) Meyers, A. I.; Sohda, T.; Loewe, M. F. J. Org. Chem. 1986, 51, 3108.
47. For total syntheses of arborescidine A, see: (a) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (b) Meyers, A. I.; Sohda, T.; Loewe, M. F. J. Org. Chem. 1986, 51, 3108.
48. For isolation of arborescidines A-D, see: Chbani, M.; Païs, M. J. Nat. Prod. 1993, 56, 99.
49. For total syntheses of arborescidine C, see: (a) Burm, B. E. A.; Meijler, M. M.; Korver, J.; Wanner, M. J. Koomen, G.-J. Tetrahedron 1998, 54, 6135. (b) Santos, L. S.; Pilli, R. A.; Rawal, V. H. J. Org. Chem. 2004, 69, 1283.
50. For total syntheses of arborescidine C, see: (a) Burm, B. E. A.; Meijler, M. M.; Korver, J.; Wanner, M. J. Koomen, G.-J. Tetrahedron 1998, 54, 6135. (b) Santos, L. S.; Pilli, R. A.; Rawal, V. H. J. Org. Chem. 2004, 69, 1283.
51. 2, see: Thomazeau, C.; Olivier-Bourbigou, H.; Magna, L.; Luts, S.; Gilbert, B. J. Am. Chem. Soc. 2003, 125, 5264.
52. Relevant procedures for all new compounds and their characterizations can be found in Supporting Information.
53. Attempts to disfavor the alleged competition were made. However, when the indole nitrogen atom in 28a was protected with Boc, the cyclization still proceeded only with PNBSA.
54. For a review on enamides, see: Rappoport, Z. The Chemistry of Enamines in The Chemistry of Functional Groups: John Wiley and Sons: New York, 1994.
55. For recent studies involving enamides, see: (a) Fuchs, J. R.; Funk, R. L. Organic Lett. 2001, 3, 3349. (b) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125.
56. For recent studies involving enamides, see: (a) Fuchs, J. R.; Funk, R. L. Organic Lett. 2001, 3, 3349. (b) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125.
57. For oxdiations of enamides, see: (a) Xiong, H.; Hsung, R. P.; Shen, L.; Hahn, J. M. Tetrahedron Lett. 2002, 43, 4449. (b) Poon, T.; Turro, N. J.; Chapman, J.; Lakshminarasimhan, P.; Lei, X.; Jockusch, S.; Franz, R.; Washington, I.; Adam, W.; Bosio, S. G. Org. Lett. 2003, 5, 4951.
58. For oxdiations of enamides, see: (a) Xiong, H.; Hsung, R. P.; Shen, L.; Hahn, J. M. Tetrahedron Lett. 2002, 43, 4449. (b) Poon, T.; Turro, N. J.; Chapman, J.; Lakshminarasimhan, P.; Lei, X.; Jockusch, S.; Franz, R.; Washington, I.; Adam, W.; Bosio, S. G. Org. Lett. 2003, 5, 4951.
59. Specific carbon numbering systems were based on Païs's isolation paper: see ref 16.
60. Smith, A. B., III; Kim. D.-S. Org. Lett. 2004, 6, 1493.
61. Heathcock, C. H.; Blumenkopf, T. A.; Smith, K. M. J. Org. Chem. 1989, 54, 1548.
62. A minor isomer was observed during the aminal formation and believed to be desbromoarborescidine D, which is diastereomeric at C-17. It was not vigorously characterized given the small quantity.
63. Hsung, R. P.; Cole, K. P.; Zehnder, L. R.; Wang, J.; Wei, L.-L.; Yang, X.-F.; Coverdale, H. A. Tetrahedron 2003, 59, 311.