First synthesis of marine alkaloid (±)-bengacarboline

Synlett

Volumn , Issue 10, 2003, Pages 1488-1490

  Pouilhès, Annie ^a   Langlois, Yves ^a   Chiaroni, Angèle ^a  

^a CNRS   (France)

Author keywords

Alkaloid; Cyclization; Imine; Indole; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; BENGACARBOLINE; CARBOXYLIC ACID DERIVATIVE; GYRASE INHIBITOR; INDOL 3 CARBOXYLIC ACID; TRYPTAMINE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MARINE ENVIRONMENT; REACTION ANALYSIS;

EID: 0041568539     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40836     Document Type: Article

References (14)

1. Foderato, T. A.; Barrows, L. R.; Lassota, P.; Ireland, C. M. J. Org. Chem. 1997, 62, 6064.
2. For a review concerning the Pictet-Spengler cyclization, see: Cox, E. D. ; Cook, J. M. Chem. Rev. 1995, 95, 1797.
3. (a) Mouhaddid, A.; Joseph, B.; Hasnaoui, A.; Mérour, J.-Y. Synthesis 2000, 549.
4. (b) Bennasar, M. L.; Roca, T.; Griera, R.; Bassa, M.; Bosh, J. J. Org. Chem. 2002, 67, 6268.
5. 3, see: Sharma, S. D.; Kanwar, S. Indian J. Chem., Sect. B 1998, 37, 965.
6. For a related reaction, see: (a) Siddiqui, S.; Siddiqui, B. S.; Naeed, A.; Begum, S.; Khan, K. A.; Ahmad, A. Fitoterapia 1990, 5, 425. (b) Faizi, S.; Naz, A. Tetrahedron 2002, 58, 6185.
7. For a related reaction, see: (a) Siddiqui, S.; Siddiqui, B. S.; Naeed, A.; Begum, S.; Khan, K. A.; Ahmad, A. Fitoterapia 1990, 5, 425. (b) Faizi, S.; Naz, A. Tetrahedron 2002, 58, 6185.
8. 2, EtOAc-heptane 40:60) affording imine 10 (197 mg, 67%).
9. For other examples of Pictet-Spengler cyclization between indole and ketimine, see: (a) Spadoni, G.; Balsamini, C.; Bedini, A.; Duranti, E.; Tontini, A. J. Heterocycl. Chem. 1992, 29, 305. (b) Rodriguez, J. G.; Gil-Lopetegui, P. J. Heterocycl. Chem. 1993, 30, 373, (c) Carrasco, N.; Urzua, A.; Cassels, B. K. J. Org. Chem. 1973, 38, 4342.
10. For other examples of Pictet-Spengler cyclization between indole and ketimine, see: (a) Spadoni, G.; Balsamini, C.; Bedini, A.; Duranti, E.; Tontini, A. J. Heterocycl. Chem. 1992, 29, 305. (b) Rodriguez, J. G.; Gil-Lopetegui, P. J. Heterocycl. Chem. 1993, 30, 373, (c) Carrasco, N.; Urzua, A.; Cassels, B. K. J. Org. Chem. 1973, 38, 4342.
11. For other examples of Pictet-Spengler cyclization between indole and ketimine, see: (a) Spadoni, G.; Balsamini, C.; Bedini, A.; Duranti, E.; Tontini, A. J. Heterocycl. Chem. 1992, 29, 305. (b) Rodriguez, J. G.; Gil-Lopetegui, P. J. Heterocycl. Chem. 1993, 30, 373, (c) Carrasco, N.; Urzua, A.; Cassels, B. K. J. Org. Chem. 1973, 38, 4342.
12. 5 [M + H]: 446.2345. Found: 446.2347.
13. 2, EtOAc-heptane 50:50) affording compound 12 in 73% yield.
14. The details of X-ray structure of compound 12 (Figure 1) will be given in a full paper (Service de cristallochimie, Institut de Chimie des Substances Naturelles).