The first total synthesis of (±)-ribasine

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1413-1416

  Ollero, Lourdes ^a   Castedo, Luis ^a   Domínguez, Domingo ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; INDANONE DERIVATIVE; PLANT EXTRACT; TOLUENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0032510366     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10778-X     Document Type: Article

References (13)

1. 1. Boente, J. M.; Castedo, L.; Cuadros, R.; Saá, J. M.; Suau, R.; Perales, A.; Martínez-Ripoll, M.; Fayos, J. Tetrahedron Lett. 1983, 24, 2029.
2. 2. Allais, D. P.; Guineaudeau, H.; Freyer, A. J.; Shamma, M.; Canguli, N. C.; Talapatra, B.; Talapatra, S. K. Tetrahedron Lett. 1983, 24, 2445.
3. 3. Boente, J. M.; Campello, M. J.; Castedo, L.; Domínguez, D.; Saá, J. M.; Suau, R.; Vidal, M. C. Tetrahedron Lett. 1983, 24, 4481.
4. 4. Allais, D. P.; Guineaudeau, H. J. Nat. Prod. 1990, 53, 1280.
5. 5. Ollero, L.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1997, 38 , 5723.
6. 6. Paleo, M. R.; Castedo, L.; Domínguez, D. J. Org. Chem. 1993, 58, 2763.
7. 7. Kanda, T.; Kato, S.; Sugino, T.; Kambe, N.; Ogawa, A.; Sonoda, N. Synthesis 1995, 1102.
8. 8. Sinnababu, A. K.; Borchardt, R. T. J. Org. Chem. 1983, 48, 2356.
9. 9. All new compounds were fully characterized spectroscopically and had satisfactory elemental analyses or molecular weights by high-resolution mass spectra.
10. 2), 103.82 (CH), 105.47 (CH), 111.10 (CH), 112.52 (C), 119.85 (CH), 120.07 (CH), 120.12 (CH), 125.22 (CH), 125.68 (CH), 126.12 (CH), 127.23 (CH), 127.84 (CH), 127.89 (CH), 128.18 (CH), 128.26 (CH), 128.49 (CH), 130.40 (C), 133.21 (C), 136.42 (C), 139.92 (C), 140.63 (C), 144.44 (C), 146.87 (C), 147.81 (C), 147.96 (C), 148.24 (C), 148.60 (C), 150.93 (C), 163.72 (CO).
11. 11. Ollero, L.; Castedo. L.; Domínguez, D. Synlett 1997, 1047.
12. 2), 103.96 (CH), 105.24 (CH), 109.34 (C), 112.75 (CH), 119.67 (CH), 120.02 (CH), 120.26 (CH), 124.76 (CH), 125.50 (CH), 125.94 (CH), 127.22 (CH), 127.67 (CH), 128.13 (CH), 128.46 (CH), 128.61 (CH), 131.18 (C), 133.10 (C), 135.16 (C), 139.69 (C), 141.03 (C), 145.11 (C), 146.80 (C), 148.22 (C), 148.50 (C), 149.39 (C), 151.02 (C), 162.00 (CO).
13. 2O in MeOH followed by treatment with sodium borohydride at reflux for one hour.