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3
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77957066564
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Manske, R. H. F., Ed.; Academic Press: New York
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(c) Ritchie, E.; Taylor, W. C. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 529. For X-ray crystallographic studies on himbacine see: Fridrichsons, J.; Mathieson, A. M. Acta Crystallogr. 1962, 15, 119.
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Ritchie, E.1
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77957066564
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(c) Ritchie, E.; Taylor, W. C. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 529. For X-ray crystallographic studies on himbacine see: Fridrichsons, J.; Mathieson, A. M. Acta Crystallogr. 1962, 15, 119.
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Fridrichsons, J.1
Mathieson, A.M.2
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5
-
-
0345353378
-
-
note
-
(d) Himbacine was isolated from the bark of Galbulimima baccata which is a member of the magnolia family, and not a pine tree as stated earlier. See ref 5b, footnote 6.
-
-
-
-
6
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0025300796
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(a) Darroch, S. A.; Taylor, W. C.; Choo, L. K; Mitchelson, F. Eur. J. Pharmacol. 1990, 182, 131.
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7
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0028874084
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(b) Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1995, 5, 61 and references therein.
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Malaska, M.J.1
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8
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12
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0029860641
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(a) For a preliminary communication of the total synthesis of himbacine, see: Chackalamannil, S.; Davies, R. J.; Asberom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812.
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Chackalamannil, S.1
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Leone, D.5
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13
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0029084209
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(b) For another total synthesis of himbacine, see: Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369. Also see: Hart, D. J.; Li, J.; Wu, W.-L.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023. For studies directed toward the total synthesis of himbacine, see:
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Hart, D.J.1
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14
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0030757959
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(b) For another total synthesis of himbacine, see: Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369. Also see: Hart, D. J.; Li, J.; Wu, W.-L.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023. For studies directed toward the total synthesis of himbacine, see:
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Hart, D.J.1
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Hofman, S.1
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17
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0000048482
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Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
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For reviews on intramolecular Diels - Alder reaction, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 513.
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Roush, W.R.1
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0003009874
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Dauben, W. G., Ed.; John Wiley & Sons: New York
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Ciganek, E.1
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(e) For a discussion of the substituent effect on intramolecular Diels - Alder reactions of enoates see: Jung, M. E. Synlett 1990, 4, 186.
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Jung, M.E.1
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22
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0000588073
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and references therein
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1,3 strain induced facial selectivity of intermolecular Diels - Alder reactions, see: Adam, W.; Glaser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190 and references therein.
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Adam, W.1
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1,3 strain-induced stereoselectivity see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
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(a) Torsell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Organic Nitro Chemistry Series; Feuer, H., Ed.; VCH Publishers: New York, 1988.
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Torsell, K.B.G.1
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0002899589
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Curran, D. P., Ed.; JAI Press Inc.: Greenwich, CT
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(b) Padwa, A.; Schoffstall, A. M. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press Inc.: Greenwich, CT, 1990; Vol. 3, p 1.
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Padwa, A.1
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0001147462
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Tetrahedron Organic Chemistry Series; Baldwin, J. E., Magnus, P., Eds.; Pergamon Press: Oxford
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(c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series; Baldwin, J. E., Magnus, P., Eds.; Pergamon Press: Oxford, 1990; Vol. 8, p 269.
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Carruthers, W.1
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37049079163
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Adams, D. R.; Carruthers, W.; Williams, M. J.; Crowley, P. J. J. Chem. Soc., Perkin Trans. 1 1989, 1507.
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Crowley, P.J.4
-
30
-
-
0345353370
-
-
note
-
(S)-3-Butyn-2-ol was purchased from Chiroscience Ltd, Cambridge Science Park, Milton Rd, Cambridge CB4 4WE, England. It is also available from DSM Fine Chemicals, 217 Route 46 W, Saddle Brook, NJ 07663-6253.
-
-
-
-
32
-
-
0000297958
-
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Brown, H. C.; Blue, C. D.; Nelson, D. J. Bhat, N. G. J. Org. Chem. 1989, 54, 6064.
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Brown, H.C.1
Blue, C.D.2
Nelson, D.J.3
Bhat, N.G.4
-
35
-
-
84877274207
-
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(d) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27(2), 127.
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Org. Prep. Proc. Int.
, vol.27
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Rossi, R.1
Carpita, A.2
Bellina, F.3
-
36
-
-
0000509322
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
-
(e) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 521.
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Sonogashira, K.1
-
37
-
-
0542418919
-
-
Tanikaga, R.; Nozaki, Y.; Tamura, T.; Kaji, A. Synthesis 1983, 134.
-
(1983)
Synthesis
, pp. 134
-
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Tanikaga, R.1
Nozaki, Y.2
Tamura, T.3
Kaji, A.4
-
38
-
-
0344059731
-
-
note
-
4a in comparison to compound 19.
-
-
-
-
39
-
-
0344922015
-
-
note
-
9 double bond.
-
-
-
-
40
-
-
0345353369
-
-
note
-
Isohimbacine (1a) did not undergo isomerization to himbacine (1) under several attempted conditions.
-
-
-
-
41
-
-
0344922014
-
-
note
-
4 proton by the piperidine nitrogen.
-
-
-
-
42
-
-
0031000573
-
-
Doller, D.; Davies, R.; Chackalamannil, S. Tetrahedron: Asymmetry 1997, 8, 1275.
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(1997)
Tetrahedron: Asymmetry
, vol.8
, pp. 1275
-
-
Doller, D.1
Davies, R.2
Chackalamannil, S.3
-
43
-
-
0344059730
-
-
note
-
The workup procedure involved addition of excess of ammonium hydroxide. This step converted the unreacted reagent, which coeluted with the product, to more polar tert-butyl urethane.
-
-
-
-
45
-
-
33845373603
-
-
Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
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J. Am. Chem. Soc.
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Takai, K.1
Nitta, K.2
Utimoto, K.3
-
46
-
-
0344490952
-
-
note
-
The technical grade chromous chloride (95%) available from Aldrich was used. Chromous chloride of high purity (99.9%), purchased from Strem Chemicals, gave inferior yields.
-
-
-
-
47
-
-
0001071162
-
-
Prolonged reaction time resulted in the formation of substantial amounts of N-deprotected free amine corresponding to 33, which could be readily converted to 33 by treatment of the crude reaction mixture with Boc anhydride in the presence of 20% aqueous sodium hydroxide. Thermolytic deprotection of the tert-butoxycarbonyl protecting group on indoles and pyrroles has been reported: Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141.
-
(1985)
Tetrahedron Lett.
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, pp. 6141
-
-
Rawal, V.H.1
Cava, M.P.2
-
48
-
-
0345353368
-
-
note
-
A large excess (8-12 wt equiv) of Raney nickel was necessary. Commercially available (Aldrich) Raney nickel was washed as mentioned before (ref 17) prior to use.
-
-
-
-
49
-
-
0345353367
-
-
note
-
3)].
-
-
-
-
50
-
-
0344922012
-
-
note
-
3)].
-
-
-
-
51
-
-
0344922011
-
-
note
-
3)].
-
-
-
-
53
-
-
0028898970
-
-
(b) Ku, Y.-Y.; Patel; Elisseou, E. M.; Sawick, D. P. Tetrahedron Lett. 1995, 36, 2733.
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Tetrahedron Lett.
, vol.36
, pp. 2733
-
-
Ku, Y.-Y.1
Patel2
Elisseou, E.M.3
Sawick, D.P.4
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