Enantioselective synthesis of the pyrroloquinoline core of the martinellines

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1395-1397

  Nieman, James A ^a   Ennis, Michael D ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MARTINELLINE; PYRROLE DERIVATIVE; PYRROLOQUINOLINE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MEDICINAL PLANT; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PLANTS, MEDICINAL; PYRROLES; QUINOLINES; STEREOISOMERISM;

EID: 0034682138     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0057030     Document Type: Article

References (23)

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7. Kang, S. K.; Park, S. S.; Kim, S. S.; Choi, J.-K.; Yum, E. K. Tetrahedron Lett. 1999, 40, 4379. Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron Lett. 1999, 40, 3339. Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj, R. P.; Lough, A. J. Chem. Commun. 1999, 651. Lovely, C. J.; Mahmud, H. Tetrahedron Lett. 1999, 40, 2079. Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215. Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287. Gurjar, M. K.; Pal, S.; Rao, A. V. R. Heterocycles 1997, 45, 231. Frank, K. E.; Aubé, J. J. Org. Chem. 2000, 65, 655.
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13. For the synthesis of 7a and 7b, see: Ravina, E.; Fueyo, J.; Teran, C.; Cid, J.; Garcia Mera, G.; Orallo, F.; Bardan, B. Pharmazie 1992, 47, 574. Barlocco, D.; Pinna, G. A.; Carboni, L.; Cipolla, P. Farmaco 1989, 44, 967. Fontenla, J. A.; Osuna, J.; Rosa, E.; Castro, M. E.; G-Ferreiro, T.; Loza-García, I.; Calleja, J. M.; Sanz, F.; Rodríquez, J.; Raviña, E.; Fueyo, J.; F-Masaguer, C.; Vidal, A.; de Ceballos, M. L. J. Med. Chem. 1994, 37, 2564.
14. 6 proton.
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20. We have applied this palladium-catalyzed carbonylative cyclization chemistry to the synthesis of related heterocycles. Further details of this interesting transformation will be reported shortly.
21. 2O as the nucleophile instead of methanol in the carbonylative cyclization reaction with 12 generated 13b directly, purification from other carboxylic acid byproducts proved to be problematic.
22. Compounds 15a and 15b can be subjected separately or as a crude mixture to the elimination protocol. When the crude mixture was used, an improved three-step yield of 67% for 16 was realized.
23. As with compounds 11a and 11b, compounds 16 and 3 displayed the ring-fusion proton coupling constant typical for a cis-fused product (J = 6.8 and 6.3 Hz, respectively). See also ref 1.