References
- Hanka , L. J. , Dietz , A. , Gerpheide , S. A. , Kuentzel , S. L. and Martin , D. G. 1978 . J. Antibiot. , 31 : 1211
- McGovren , J. P. , Clarke , G. L. , Pratt , E. A. and DeKoning , T. F. 1984 . J. Antibiot. , 37 : 63
- Rawal , V. H. , Jones , R. J. and Cava , M. P. 1987 . Heterocycles , 25 : 701
- Castedo , L. , Marcos , C. F. , Ruíz , M. and Tojo , G. 1990 . Heterocycles , 31 : 37
- Atta-ur-Rahman , ed. 1989 . Vol. 3 , 301 – 383 . Elsevier . For a review on the properties and synthesis of CC-1065, PDE-I and PDE-II, see Coleman, R.S. and Boger, D.L.in “Studies in Natural Products Chemistry”
- Tischler , A. N. and Lanza , T. J. 1986 . Tetrahedron Lett. , 27 : 1653
- Boger , D. L. , Cerbone , L. R. and Yohannes , D. 1988 . J. Org. Chem. , 53 : 5163
- Marcos , C. F. 1991 . Spain : Ph.D. Thesis, University of Santiago de Compostela . Different nitrating and nitrosating conditions were tested, both in acid and basic media, and using one or two phase systems. For further details see:
- The indoline 7a was readily prepared from the corresponding indole 3 by reduction with magnesium in methanol.10 The indolines 7b and 7c were prepared by reduction of the O-benzyl derivative of 3 followed by protection of the nitrogen with either acetic anhydride or trifluoroacetic anhydride in pyridine, and debenzylation by catalytic hydrogenation on Pd-C. These indolines show the following 1H NMR signals in CDCl3
- 7a Δ: 9.0 (br s, 1 H, -NH), 6.27 (s, 1HH5), 5.5 (br s, 1H, Ar-OH), 4.48 (t, J=5.6 Hz, 1H, -CH2-CH-(OCH3)2), 4.41 (dd, J=6.5 and 5.5 Hz, 1HH2), 3.83 (s, 3H, -COOCH 3), 3.76 (s, 3H, Ar-OCH 3), 3.33 (d, J=3.0 Hz, 6H, -CH2-CH-(OCH 3)2), 3.29 (d, J=5.9 Hz, 2HH3) and 2.71 (d, J=5.6 Hz, 2H, -CH2-CH-(OCH3)2) ppm
- 7b Δ: 6.62 (s, 1H, ArH), 5.88 (br s, 1H, ArOH), 5.42 (d, 1HH 2), 4.46 (t, J=5.4 Hz, 1H, -CH2-CH-(OCH3)2), 3.80 (s, 3H, -COOCH 3), 3.70 (s, 3H, Ar-OCH 3), 3.38 (m, 1HH 3), 3.33 (d, J=4.5 Hz, 6H, -CH2-CH-(OCH 3)2), 3.07 (dd, J=15.8 and 1.5 Hz, 1HH3), 2.74 (d, J=5.5 Hz, 2H, -CH 2-CH 2-CH3)2) and 2.30 (s, 3H, -COCH 3) ppm.
- 7c Δ: 6.72 (s, 1H, ArH), 5.20 (d, J=9.0 Hz, 1HH2), 4.42 (t, J=5.4 Hz, 1H, -CH2-CH-(OCH3)2), 3.78 (s, 3H, -COOCH 3), 3.75 (s, 3H, Ar-OCH 3), 3.53 (dd, J=15.8 and 9.0 Hz, 1HH3), 3.32 (d, J=5.0 Hz, 6H, -CH2-CH-(OCH 3)2), 3.24 (d, J=15.8 Hz, 1HH3) and 2.74 (d, J=5.4 Hz, 2H, -CH2-CH-(OCH3)2) ppm.
- Martin , P. 1989 . Helv. Chim. Acta , 72 : 1554
- When indole 3 or indoline 7a were subjected to reaction with p-toluensulphonylazide and sodium hydride in diethyl ether, in both cases the corresponding tosyl protected phenol was obtained as the only product. No formation of the desired diazocompounds was observed, in variance with reported reactions with similar compounds.12
- Tedder , J. M. and Webster , B. 1960 . J. Chem. Soc. , 4417
- See previous paper in this journal.
- Barton , D. H. R. , Géro , S. D. , Augy , S. and Quiclet-Sire. , B. 1986 . J. Chem. Soc., Chem Commun. , : 1399
- Barton , D. H. R. , Camara , J. , Dalko , P. , Géro , S. D. , Quiclet-Sire , B. and Stütz. , P. 1989 . J. Org. Chem. , 54 : 3764
- Hemetsberger , H. and Knittel , D. H. 1970 . Weidmann. Monatsh. Chem. , 101 : 161
- Bolton , R. E. , Moody , C. J. , Rees , C. W. and Tojo , G. 1987 . J. Chem. Soc., Perkin Trans. I , 931
- Garegg , B. and Samuelsson , J. 1979 . Chem. Soc., Chem. Commun. , 978
- Fieser , L. F. and von E. Doering , W. 1946 . J. Am. Chem. Soc. , 68 : 2252
- Ferris , A. F. , Mc Lean , K. W. , Marks , I. G. and Emmons , W. E. 1953 . J. Am. Chem. Soc. , 75 : 4078
- Both the iodide 18 and the nitrate 1 are quite unstable compounds. On the contrary, their O-benzyl derivatives are perfectly stable, probably due to a decrease in the electron richness of their aromatic systems relative to the free phenols 18 and 1. these O-benzyl derivatives could be obtained from indole 16 by iodo-dehydroxylation and nitrate-deiodination as in 18 and 1. All attempts to carry out a nitro transfer in the O-benzyl derivative of nitrate 1 led to recovery of starting compound.