-
1
-
-
0030995278
-
-
Patil, A. D.; Freyer, A. J.; Taylor, P. B.; Carté, B.; Zuber, G.; Johnson, R. K.; Faulkner, D. J. J. Org. Chem. 1997, 62, 1814-1819.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 1814-1819
-
-
Patil, A.D.1
Freyer, A.J.2
Taylor, P.B.3
Carté, B.4
Zuber, G.5
Johnson, R.K.6
Faulkner, D.J.7
-
2
-
-
0033996798
-
-
The identity of the sponge has been revised: Braekman, J. C.; Daloze, D.; Tavares, R.; Hajdu, E.; Van Soest, R. W. M. J Nat. Prod. 2000, 63, 193-196.
-
(2000)
J Nat. Prod.
, vol.63
, pp. 193-196
-
-
Braekman, J.C.1
Daloze, D.2
Tavares, R.3
Hajdu, E.4
Van Soest, R.W.M.5
-
4
-
-
23944434392
-
-
(a) For reviews summarizing the isolation, structure and synthesis of batzelladine alkaloids, see: Berlinck, R. G. S.; Kossuga, M. H. J. Nat. Prod. 2005, 22, 516-550 and earlier reviews in this series,
-
(2005)
J. Nat. Prod.
, vol.22
, pp. 516-550
-
-
Berlinck, R.G.S.1
Kossuga, M.H.2
-
5
-
-
27144504744
-
-
(b) For the recent isolation of a new batzelladine alkaloid, see: Gallimore, W. A.; Kelly, M.; Scheuer, P. J. J. Nat. Prod. 2005, 68, 1420-1423.
-
(2005)
J. Nat. Prod.
, vol.68
, pp. 1420-1423
-
-
Gallimore, W.A.1
Kelly, M.2
Scheuer, P.J.3
-
6
-
-
18744372132
-
-
(c) For a recent synthetic study, see: Arnold, M. A.; Duron, S. G.; Gin, D. Y. J. Am. Chem. Soc. 2005, 127, 6924-6925.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 6924-6925
-
-
Arnold, M.A.1
Duron, S.G.2
Gin, D.Y.3
-
7
-
-
0030599231
-
-
Snider, B. B.; Chen, J.; Patil, A. D.; Freyer, A. J. Tetrahedron Lett. 1996, 37, 6977-6980.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 6977-6980
-
-
Snider, B.B.1
Chen, J.2
Patil, A.D.3
Freyer, A.J.4
-
8
-
-
0033619847
-
-
Cohen, F.; Overman, L. E.; Sakata, S. K. L. Org. Lett. 1999, 1, 2169-2172.
-
(1999)
Org. Lett.
, vol.1
, pp. 2169-2172
-
-
Cohen, F.1
Overman, L.E.2
Sakata, S.K.L.3
-
9
-
-
33644636424
-
-
note
-
These data were not presented in the paper or the Supporting Information.
-
-
-
-
11
-
-
0033591151
-
-
(b) Black, G. P.; Murphy, P. J.; Thornhill, A. J.; Walshe, N. D. A.; Zanetti, C. Tetrahedron 1999, 55, 6547-6554.
-
(1999)
Tetrahedron
, vol.55
, pp. 6547-6554
-
-
Black, G.P.1
Murphy, P.J.2
Thornhill, A.J.3
Walshe, N.D.A.4
Zanetti, C.5
-
12
-
-
0035980339
-
-
(a) Our synthesis of the natural product has been outlined: Cohen, F.; Overman, L. E. J. Am. Chem. Soc. 2001, 123, 10782-10783.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 10782-10783
-
-
Cohen, F.1
Overman, L.E.2
-
14
-
-
0033612744
-
-
Coffey, D. S.; McDonald, A. I.; Overman, L. E.; Stappenbeck, F. J. Am. Chem. Soc. 1999, 121, 6944-6945.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 6944-6945
-
-
Coffey, D.S.1
McDonald, A.I.2
Overman, L.E.3
Stappenbeck, F.4
-
18
-
-
0000074967
-
-
Hassner, A.; Fibiger, R.; Andisik, D. J. J. Org. Chem. 1984, 49, 4237-4244.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 4237-4244
-
-
Hassner, A.1
Fibiger, R.2
Andisik, D.J.3
-
20
-
-
0019408557
-
-
Without this basic additive, the bis-dimethyl acetal was isolated in quantitative yield. See: Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 103, 3210-3213.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 3210-3213
-
-
Woodward, R.B.1
-
21
-
-
26844568935
-
-
Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26-28.
-
(1998)
Synlett
, pp. 26-28
-
-
Blakemore, P.R.1
Cole, W.J.2
Kocienski, P.J.3
Morley, A.4
-
23
-
-
33644656617
-
-
Volkov, A. A.; Zlotski, S. S.; Kravets, E. K.; Spirknin, L. V. Chem. Heterocycl. Compd. (Engl. Trans.) 1985, 21, 861-863.
-
(1985)
Chem. Heterocycl. Compd. (Engl. Trans.)
, vol.21
, pp. 861-863
-
-
Volkov, A.A.1
Zlotski, S.S.2
Kravets, E.K.3
Spirknin, L.V.4
-
24
-
-
0001345246
-
-
Sjiki, H.; Hattori, K.; Hirota, K. J. Org. Chem. 1998, 63, 7990-7992.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 7990-7992
-
-
Sjiki, H.1
Hattori, K.2
Hirota, K.3
-
25
-
-
0033525821
-
-
Franklin, A. S.; Ly, S. K.; Mackin, G. H.; Overman, L. E.; Shaka, A. J. J. Org. Chem. 1999, 64, 1512-1519.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1512-1519
-
-
Franklin, A.S.1
Ly, S.K.2
Mackin, G.H.3
Overman, L.E.4
Shaka, A.J.5
-
26
-
-
33751391460
-
-
Bernatowicz, M. Z.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2502.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 2497-2502
-
-
Bernatowicz, M.Z.1
Wu, Y.2
Matsueda, G.R.3
-
27
-
-
0033525676
-
-
Stereoselection in the tethered Biginelli condensation has been thoroughly investigated: McDonald, A. I.; Overman, L. E. J. Org. Chem. 1999, 64, 1520-1528.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1520-1528
-
-
McDonald, A.I.1
Overman, L.E.2
-
28
-
-
0028113629
-
-
and references therein
-
Reuman, M.; Eissenstat, M. A.; Weaver, J. D., III Tetrahedron Lett. 1994, 35, 8303-8306, and references therein.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 8303-8306
-
-
Reuman, M.1
Eissenstat, M.A.2
Weaver III, J.D.3
-
29
-
-
33644648846
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-
note
-
A model compound similar to 26 bearing a methyl ester was completely resistant to both basic and acidic hydrolysis.
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-
-
-
30
-
-
0030599231
-
-
Snider, B. B.; Chen, J.; Patil, A. D.; Freyer, A. J. Tetrahedron Lett. 1996, 37, 6977-6980.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 6977-6980
-
-
Snider, B.B.1
Chen, J.2
Patil, A.D.3
Freyer, A.J.4
-
31
-
-
0032491029
-
-
Black, G. P.; Murphy, P. J.; Walshe, N. D. A. Tetrahedron 1998, 54, 9481-9488.
-
(1998)
Tetrahedron
, vol.54
, pp. 9481-9488
-
-
Black, G.P.1
Murphy, P.J.2
Walshe, N.D.A.3
-
32
-
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33644644389
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note
-
Synthesized from unsaturated azido benzoate 15 in a fashion analogous to 29; see Supporting Information.
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-
-
-
34
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0001014077
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Heathcock, C. H.; Pietter, S.; Ruggeri, R. B.; Ragan, J. A.; Kath, J. C. J. Org. Chem. 1992, 57, 2554-2566.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 2554-2566
-
-
Heathcock, C.H.1
Pietter, S.2
Ruggeri, R.B.3
Ragan, J.A.4
Kath, J.C.5
-
39
-
-
0000370097
-
-
Taber, D. F.; Amedio, J. C.; Patel, Y. K. J. Org. Chem. 1985, 50, 3618-1619.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 3618-11619
-
-
Taber, D.F.1
Amedio, J.C.2
Patel, Y.K.3
-
40
-
-
0029084414
-
-
Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 5461-5464
-
-
Williams, J.M.1
Jobson, R.B.2
Yasuda, N.3
Marchesini, G.4
Dolling, U.-H.5
Grabowski, E.J.J.6
-
41
-
-
0001249486
-
-
Chen, K. M.; Hardmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-8.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 155-158
-
-
Chen, K.M.1
Hardmann, G.E.2
Prasad, K.3
Repic, O.4
Shapiro, M.J.5
-
42
-
-
37049134703
-
-
Atkins, P. R.; Glue, S. E. J.; Kay, I. T. J. Chem. Soc., Perkin Trans. 1 1973, 2644-2646.
-
(1973)
J. Chem. Soc., Perkin Trans. 1
, pp. 2644-2646
-
-
Atkins, P.R.1
Glue, S.E.J.2
Kay, I.T.3
-
43
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33644658289
-
-
note
-
These reactions were conducted on a small scale (<1 mg) and analyzed by HPLC-MS.
-
-
-
-
44
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-
0001300818
-
-
Mukayama, T.; Usui, M.; Shimada, E.; Saigo, K. Chem. Lett. 1975, 1045-1048.
-
(1975)
Chem. Lett.
, pp. 1045-1048
-
-
Mukayama, T.1
Usui, M.2
Shimada, E.3
Saigo, K.4
-
45
-
-
33644646041
-
-
note
-
Molecular mechanics modeling shows that the ester group of intermediates of this type exists preferentially in a conformation in which the methine hydrogen and the carbonyl π-system are nearly orthogonal. This feature is likely responsible for the failure to generate the ester enolate of 69.
-
-
-
-
46
-
-
33644662313
-
-
note
-
3SiH, TFA) either failed to reduce 71 or led to decomposition.
-
-
-
-
47
-
-
33644637301
-
-
note
-
1H NMR spectrum of 76 corresponding to the left-hand tricyclic portion were nearly identical to that of 68. The two most diagnostic peaks were the vinyl methyl singlet at δ 2.26 and the allylic methine at δ 4.25 (dd, J = 11.7, 5.2 Hz). Both of these resonances were absent from the spectrum of 75, and were replaced with an allylic methine at δ 4.49 (q, J = 6.3 Hz) and a multiplet at δ 2.45-2.30 corresponding to the allylic methylene.
-
-
-
-
48
-
-
33644647579
-
-
note
-
Details are provided in the Supporting Information.
-
-
-
-
49
-
-
0028910985
-
-
For a discussion of the McLafferty rearrangement in other batzelladine alkaloids see (a) Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; De Brosse, C.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westley, J. W.; Potts, B. C. M. J. Org. Chem. 1995, 60, 1182-1188.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1182-1188
-
-
Patil, A.D.1
Kumar, N.V.2
Kokke, W.C.3
Bean, M.F.4
Freyer, A.J.5
De Brosse, C.6
Mai, S.7
Truneh, A.8
Faulkner, D.J.9
Carte, B.10
Breen, A.L.11
Hertzberg, R.P.12
Johnson, R.K.13
Westley, J.W.14
Potts, B.C.M.15
-
50
-
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0033996798
-
-
(b) Braekman, J. C.; Daloze, D.; Tavares, R.; Hajdu, E.; Van Soest, R. W. M. J. Nat. Prod. 2000, 63, 193-196.
-
(2000)
J. Nat. Prod.
, vol.63
, pp. 193-196
-
-
Braekman, J.C.1
Daloze, D.2
Tavares, R.3
Hajdu, E.4
Van Soest, R.W.M.5
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