A divergent approach to cryptotackieine and cryptosanguinolentine alkaloids

Tetrahedron Letters

Volumn 40, Issue 40, 1999, Pages 7275-7278

  Fresneda, Pilar M ^a   Molina, Pedro ^a   Delgado, S ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Alkaloids; Aza Wittig reaction; Insertion reaction; Microwave heating; Nitrogen heterocycles

Indexed keywords

1 METHYL 3 (O AZIDOPHENYL) 2 QUINOLINONE; ALKALOID; BENZALDEHYDE; CRYPTOSANGUINOLENTINE; CRYPTOTACKIEINE; INDOLOQUINOLINE DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHONIUM DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; HEATING; HYDROGENATION; METHYLATION; PARTIAL DRUG SYNTHESIS; REDUCTION;

EID: 0033214203     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01477-X     Document Type: Article

References (17)

1. Pousset, J. L.; Jossag, A.; Boch, B. Phytochemistry 1995, 39, 735-736. Cimanga, K.; De Bruyne, T.; Pieters, L.; Claeys, M.; Vlietinck, A. Tetrahedron Lett. 1996, 37, 1703-1706. Sharaf, M. H. M.; Schiff Jr., P. L.; Tackie, A. N.; Phoebe Jr., C. H.; Martin, G. E. J. Heterocyl. Chem. 1996, 33, 239-243.
2. Pousset, J. L.; Jossag, A.; Boch, B. Phytochemistry 1995, 39, 735-736. Cimanga, K.; De Bruyne, T.; Pieters, L.; Claeys, M.; Vlietinck, A. Tetrahedron Lett. 1996, 37, 1703-1706. Sharaf, M. H. M.; Schiff Jr., P. L.; Tackie, A. N.; Phoebe Jr., C. H.; Martin, G. E. J. Heterocyl. Chem. 1996, 33, 239-243.
3. Pousset, J. L.; Jossag, A.; Boch, B. Phytochemistry 1995, 39, 735-736. Cimanga, K.; De Bruyne, T.; Pieters, L.; Claeys, M.; Vlietinck, A. Tetrahedron Lett. 1996, 37, 1703-1706. Sharaf, M. H. M.; Schiff Jr., P. L.; Tackie, A. N.; Phoebe Jr., C. H.; Martin, G. E. J. Heterocyl. Chem. 1996, 33, 239-243.
4. Cimanga, K.; De Bruyne, T.; Pieters, L.; Vlietinck, A. J. Nat. Prod. 1997, 60, 688-691.
5. Peczyriskc-Czoch, W.; Pognan, F.; Kaczmarck, L.; Boratyriski, J. J. Med. Chem. 1994, 37, 3503-3510.
6. Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197-1218.
7. Molina, P.; Alajarin, M.; Vidal, A. J. Chem. Soc., Chem. Commun. 1990, 1277-1279. Molina, P.; Alajarin, M.; Vidal, A.;Sanchez-Andrada, P. J. Org. Chem. 1992, 57, 929-939.
8. Molina, P.; Alajarin, M.; Vidal, A. J. Chem. Soc., Chem. Commun. 1990, 1277-1279. Molina, P.; Alajarin, M.; Vidal, A.; Sanchez-Andrada, P. J. Org. Chem. 1992, 57, 929-939.
9. Alajarin, M.; Molina, P.; Vidal, A. J. Nat. Prod. 1997, 60, 747-748. Timari, G.; Soós, T.; Hajós, G. Synlett 1997, 1067-1068. Molina, P.; Fresneda, P. M.; Delgado, S. Synthesis 1999, 326-329.
10. Alajarin, M.; Molina, P.; Vidal, A. J. Nat. Prod. 1997, 60, 747-748. Timari, G.; Soós, T.; Hajós, G. Synlett 1997, 1067-1068. Molina, P.; Fresneda, P. M.; Delgado, S. Synthesis 1999, 326-329.
11. Alajarin, M.; Molina, P.; Vidal, A. J. Nat. Prod. 1997, 60, 747-748. Timari, G.; Soós, T.; Hajós, G. Synlett 1997, 1067-1068. Molina, P.; Fresneda, P. M.; Delgado, S. Synthesis 1999, 326-329.
12. Ardakani, M. A.; Smalley, R. K.; Smith, R. M. J. Chem. Soc., Perkin Trans. 1 1983, 2501-2506.
13. -1. MS: m/z (%) (EI positive) 267 (M+1, 3), 266 (M, 18), 234 (14), 220 (100), 190 (13), 165 (20).
14. 2, 100), 234 (28), 219 (67).
15. 2 evolution had ceased). The tube was placed in a Synthewave 402 reactor and irradiated in following sequence: 5 min at 150°C, 5 min at 165°C and 20 min at 180°C. After cooling the precipitated solid was collected and chromatographed on a silica gel column using acetone as eluent to give 1 in 40% yield.
16. 4OH 25:25:1 as eluent to give cryptosanguinolentine 2 (42 mg, 90% yield).
17. 1 for the natural products.