Synthetic Approach to Olguine: EPC¹ Preparation of Ethyl 6,7-Anhydro-4-O-Benzyl-2,3-Dideoxy-α-D-Altro-Oct-2-Eno-1,8-Dialdo-1,5-Pyranoside

References

• Seebach , D. and Hungerbuhler , E. 1980 . Modern Synthetic. Methods , Edited by: Scheffold , R. Berlin : Salle and Sauerlander . ed.
   Google Scholar
• Alemany , A. , Marquez , G. , Pascual , C. , Valverde , S. , Perales , A. , Fayos , J. and Martínez-Ripoll , M. 1979 . Tetrahedron Lett. , : 3579
   Google Scholar
• Pettit , G. R. (Cancer Research Institute, Arizona State University), private communication.
   Google Scholar
• Valverde , S. , Herradón , B. , Rabanal , R. M. and Martín-Lomas , M. 1987 . Can. J. Chem. , 65 : 332
   Google Scholar
• Georges , M. , Mackay , D. and Fraser-Reid , B. 1984 . Con. J. Chem. , 62 : 1539
   Google Scholar
• Chaundhary , S. K. and Hernandez , O. 1979 . Tetrahedron Lett. , : 99
   Google Scholar
• All new compounds gave satisfactory spectroscopic and analytical data, except 10, which gave only satisfactory spectroscopic (1H NMR) data.
   Google Scholar
• Czernecki , C. , Georgoulis , C. and Provelenghiou , C. 1976 . Tetrahedron Lett. , : 3535
   Google Scholar
• Corey , E. J. and Suggs , J. W. 1975 . Tetrahedron Lett. , : 2647
   Web of Science ®Google Scholar
• Herscovici , J. and Antonakis , K. 1980 . J. C. S. Chem. Comm. , : 561
   Google Scholar
• Isler , O. , Gutman , H. , Montavon , M. , Ruegg , R. , Ryset , G. and Zeller , P. 1957 . Helv. Chim. Acta , 40 : 1249
   Google Scholar
• Valverde , S. , Martín-Lomas , M. and Herradon , B. 1987 . Tetrahedron , 43 : 1895
   Google Scholar
• Sharpless , K. B. and Michaelson , R. C. 1973 . J. Am. Chem. Soc. , 95 : 6136
   Web of Science ®Google Scholar
• Spectroscopic data: 14: |α|25D = -187[ddot] (CHCl3, c = 0.2). 1H NMR (CDCl3): δ 1.20 (3H, t, J = 6 Hz, H-10), 2.15 (1H, s, broad, exchangeable with D2O, OH), 3.10–3.95 (8H, m), 4.50 (1H, d, J = 12 Hz, OCH2Ph), 4.70 (1H, d, J = 12 Hz, OCH2Ph), 5.10 (1H, d, J = 2 Hz, H-1), 6.05 (2H, m, H-2. H-3), 7.25 (5H, s, aromatics) ppm. 13C NMR (20 MHz) (CDCl3): δ 138.2, 130.1, 128.5, 128.1, 120.1 (aromatics and olefinics), 93.8 (C-1), 70.9 (C-11), 70.1 (C-4), 67.6 (C-5), 64.0 (C-9), 60.7 (C-8), 56.8 (C-7)∗, 55.7 (C-6), 15.3 (C-10) ppm. 15: |α|25D=-143[ddot] (CHCl3, c - 0.1). 1H NMR (CDCl3): δ 1.17 (3H, t, J = 6 Hz), 1.84 (1H, s broad, exchangeable with D2O, OH), 3.43 (4H, m), 3.80 (4H, m), 4.63 (2H, s, OCH2Ph), 4.97 (1H, d, J = 2 Hz, H-1), 5.98 (2H, m, H-2, H-3), 7.30 (5H, s, aromatics) ppm. 13C NMR (20 MHz) (CDCl3): 6 137.9, 129.3, 128.5, 128.4, 127.9, 127.7, 126.7 (aromatics and olefinics), 93.9 (C-1), 71.7 (C-11), 68.4 (C-4)∗, 67.5 (C-5)∗, 64.2 (C-9)∗, 61.0 (C-8), 56.7 (C-7), 54.2 (C-6), 15.2 (C-11) ppm. ∗Exchangeable signals. 15. Spectroscopic data. 4: |α|25D = -173[ddot] (CHCl3, c = 0.15). 1H NMR (90 MHz) (CDCl3) δ 1.10 (3H, t, J = 6 Hz, H-10), 3.35–3.70 (4H, m, H-6, H-7, H-9a, H-9b), 3.75 (1H, dd, J = 5 Hz, 3 Hz, H-5), 4.10 (1H, dd, J = 5 Hz, 3 Hz, H-4), 4.55 (2H, s, H-11), 4.90 (1H, d, J = 3 Hz, H-1), 5.70–6.20 (2H, m, H-2, H-3), 7.30 (5H, s, aromatics), 9.45 (1H, d, J = 5 Hz, H-8) ppm. 13C NMR (20 MHz) (CDCl3) 6 197.5 (C-8),138.1, 133.8, 129.8, 128.5, 127.8, 126.2 (aromatics and olefinics), 93.8 (C-1), 71.2 (C-11), 67.7 (C-4), 67.4∗ (C-5), 64.1 (C-9), 57.7∗ (C-6), 15.1 (C-10) ppm. 16: |α|25D = -117[ddot] (CHCl3, c = 0.32). 1H NMR (90 MHz) (CDCl3) δ 1.15 (3H, t, J = 7 Hz, H-10), 3.25–3.85 (5H, m, H-5, H-6, H-7, H-9a, H-9b), 4.15 (1H, dd, J = 5 Hz, 3 Hz, H-4), 4.45 (1H, d, J = 18 Hz, H-11a), 4.55 (1H, d, J = 18 Hz, H-11b), 5.10 (1H, d, J = 2 Hz, H-1), 5.95-6.10 (2H, m, H-2, H-3), 7.30 (5H, s, aromatics), 9.40 (1H, d, J = 5 Hz, H-8) ppm. 13c NMR (20 MHz) (CDCl3) δ 198.0 (C-8), 138.0, 129.9, 128.5. 127.9, 125.9 (aromatics and olefinics), 94.0 (C-1), 70.9 (C-11), 68.3∗ (C-4), 68.0∗ (C-5). 64.2 (C-9), 58.9 (C-7), 56.6 (C-6), 15.2 (C-10) ppm. ∗Exchangeable signals.
   Google Scholar
• Katsuki , T. and Sharpless , K. B. 1980 . J. Am. Chem. Soc. , 102 : 5974
   Web of Science ®Google Scholar
• Valverde , S. unpublished results.
   Google Scholar