-
1
-
-
0033740808
-
-
Matsumura, T.; Kasai, M.; Hayashi, T.; Arisawa, M.; Momose, Y.; Arai, I.; Amagaya, S.; Komatsu, Y. Pharm. Biol. 2000, 38, 302-307.
-
(2000)
Pharm. Biol
, vol.38
, pp. 302-307
-
-
Matsumura, T.1
Kasai, M.2
Hayashi, T.3
Arisawa, M.4
Momose, Y.5
Arai, I.6
Amagaya, S.7
Komatsu, Y.8
-
2
-
-
42249087299
-
-
Davis, A. D.; Ritthiwigrom, T.; Pyne, S. G. Tetrahedron 2008, 64, 4868-4879.
-
(2008)
Tetrahedron
, vol.64
, pp. 4868-4879
-
-
Davis, A.D.1
Ritthiwigrom, T.2
Pyne, S.G.3
-
3
-
-
51649092172
-
-
For a preliminary communication on the synthesis of, -uniflorine
-
For a preliminary communication on the synthesis of (+)-uniflorine A, see: Ritthiwigrom, T.; Pyne, S. G. Org. Lett. 2008, 10, 2769-2771.
-
(2008)
Org. Lett
, vol.10
, pp. 2769-2771
-
-
see, A.1
Ritthiwigrom, T.2
Pyne, S.G.3
-
4
-
-
0027973729
-
-
Nash, R. J.; Thomas, P. I.; Waigh, R. D.; Fleet, G. W. J.; Wormald, M. R.; de Q. Lilley, P. M.; Watkin, D. J. Tetrahedron Lett. 1994, 35, 7849-7852.
-
(1994)
Tetrahedron Lett
, vol.35
, pp. 7849-7852
-
-
Nash, R.J.1
Thomas, P.I.2
Waigh, R.D.3
Fleet, G.W.J.4
Wormald, M.R.5
de, Q.6
Lilley, P.M.7
Watkin, D.J.8
-
5
-
-
0024245410
-
-
Molyneux, R. J.; Benson, M.; Wong, R. Y.; Tropea, J. E.; Elbein, A. D. J. Nat. Prod. 1988, 51, 1198-1206.
-
(1988)
J. Nat. Prod
, vol.51
, pp. 1198-1206
-
-
Molyneux, R.J.1
Benson, M.2
Wong, R.Y.3
Tropea, J.E.4
Elbein, A.D.5
-
6
-
-
0023711473
-
-
Nash, R. J.; Fellows, L. E.; Plant, A. C.; Fleet, G. W. J.; Derome, A. E.; Baird, P. D.; Hegarty, M. P.; Scofield, A. M. Tetrahedron 1988, 44, 5959-5964.
-
(1988)
Tetrahedron
, vol.44
, pp. 5959-5964
-
-
Nash, R.J.1
Fellows, L.E.2
Plant, A.C.3
Fleet, G.W.J.4
Derome, A.E.5
Baird, P.D.6
Hegarty, M.P.7
Scofield, A.M.8
-
7
-
-
84889429748
-
-
Fattorusso, E, Taglialatela-Scafati, O, Eds, Wiley-VCH Verlag: Weinheim, Germany
-
Asano, N. In Modern Alkaloids: Structure, Isolation, Synthesis and Biology; Fattorusso, E., Taglialatela-Scafati, O., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 2008; pp 111-138.
-
(2008)
Modern Alkaloids: Structure, Isolation, Synthesis and Biology
, pp. 111-138
-
-
Asano, N.1
-
8
-
-
0023894613
-
-
Nash, R. J.; Fellows, L. E.; Dring, J. V.; Fleet, G. W. J.; Derome, A. E.; Hamor, T. A.; Scofield, A. M.; Watkin, D. J. Tetrahedron Lett. 1988, 29, 2487-2490.
-
(1988)
Tetrahedron Lett
, vol.29
, pp. 2487-2490
-
-
Nash, R.J.1
Fellows, L.E.2
Dring, J.V.3
Fleet, G.W.J.4
Derome, A.E.5
Hamor, T.A.6
Scofield, A.M.7
Watkin, D.J.8
-
9
-
-
0037423121
-
-
Kato, A.; Kano, E.; Adachi, I.; Molyneux, R. J.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Wormald, M. R.; Kizu, H.; Ikeda, K.; Asano, N. Tetrahedron: Asymmetry 2003, 14, 325-331.
-
(2003)
Tetrahedron: Asymmetry
, vol.14
, pp. 325-331
-
-
Kato, A.1
Kano, E.2
Adachi, I.3
Molyneux, R.J.4
Watson, A.A.5
Nash, R.J.6
Fleet, G.W.J.7
Wormald, M.R.8
Kizu, H.9
Ikeda, K.10
Asano, N.11
-
10
-
-
33751106710
-
-
Van Ameijde, J.; Horne, G.; Wormald, M. R.; Dwek, R. A.; Nash,R. J.; Jones, P. W.; Evinson, E. L.; Fleet, G. W. J. Tetrahedron: Asymmetry 2006, 17, 2702-2712.
-
(2006)
Tetrahedron: Asymmetry
, vol.17
, pp. 2702-2712
-
-
Van Ameijde, J.1
Horne, G.2
Wormald, M.R.3
Dwek, R.A.4
Nash, R.J.5
Jones, P.W.6
Evinson, E.L.7
Fleet, G.W.J.8
-
11
-
-
0030498371
-
-
Wormald, M. R.; Nash, R. J.; Watson, A. A.; Bhadoria, B. K.; Langford, R.; Sims, M.; Fleet, G. W. J. Carbohydr. Lett. 1996, 2, 169-174.
-
(1996)
Carbohydr. Lett
, vol.2
, pp. 169-174
-
-
Wormald, M.R.1
Nash, R.J.2
Watson, A.A.3
Bhadoria, B.K.4
Langford, R.5
Sims, M.6
Fleet, G.W.J.7
-
12
-
-
0033000375
-
-
Kato, A.; Adachi, I.; Miyauchi, M.; Ikeda, K.; Komae, T.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Wormald, M. R.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 1999, 316, 95-103.
-
(1999)
Carbohydr. Res
, vol.316
, pp. 95-103
-
-
Kato, A.1
Adachi, I.2
Miyauchi, M.3
Ikeda, K.4
Komae, T.5
Kizu, H.6
Kameda, Y.7
Watson, A.A.8
Nash, R.J.9
Wormald, M.R.10
Fleet, G.W.J.11
Asano, N.12
-
13
-
-
17744416590
-
-
Asano, N.; Kuroi, H.; Ikeda, K.; Kizu, H.; Kameda, Y.; Kato, A.; Adachi, I.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1-8.
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 1-8
-
-
Asano, N.1
Kuroi, H.2
Ikeda, K.3
Kizu, H.4
Kameda, Y.5
Kato, A.6
Adachi, I.7
Watson, A.A.8
Nash, R.J.9
Fleet, G.W.J.10
-
14
-
-
0036929215
-
-
Yamashita, T.; Yasuda, K.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Asano, N. J. Nat. Prod. 2002, 65, 1875-1881.
-
(2002)
J. Nat. Prod
, vol.65
, pp. 1875-1881
-
-
Yamashita, T.1
Yasuda, K.2
Kizu, H.3
Kameda, Y.4
Watson, A.A.5
Nash, R.J.6
Fleet, G.W.J.7
Asano, N.8
-
15
-
-
34447314459
-
-
Kato, A.; Kato, N.; Adachi, I.; Hollinshead, J.; Fleet, G. W. J.; Kuriyama, C.; Ikeda, K.; Asano, N.; Nash, R. J. J. Nat. Prod. 2007, 70, 993-997.
-
(2007)
J. Nat. Prod
, vol.70
, pp. 993-997
-
-
Kato, A.1
Kato, N.2
Adachi, I.3
Hollinshead, J.4
Fleet, G.W.J.5
Kuriyama, C.6
Ikeda, K.7
Asano, N.8
Nash, R.J.9
-
16
-
-
2542511633
-
-
Asano, N.; Ikeda, K.; Kasahara, M.; Arai, Y.; Kizu, H. J. Nat. Prod. 2004, 67, 846-850.
-
(2004)
J. Nat. Prod
, vol.67
, pp. 846-850
-
-
Asano, N.1
Ikeda, K.2
Kasahara, M.3
Arai, Y.4
Kizu, H.5
-
17
-
-
0033592505
-
-
For previous syntheses of casuarine see
-
For previous syntheses of casuarine see: Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311-1314.
-
(1999)
Org. Lett
, vol.1
, pp. 1311-1314
-
-
Denmark, S.E.1
Hurd, A.R.2
-
19
-
-
20444438808
-
-
Izquierdo, I.; Plaza, M. T.; Tamayo, J. A. Tetrahedron 2005, 61, 6527-6533.
-
(2005)
Tetrahedron
, vol.61
, pp. 6527-6533
-
-
Izquierdo, I.1
Plaza, M.T.2
Tamayo, J.A.3
-
20
-
-
60749132180
-
-
Cardona, F.; Parmeggiani1, C.; Faggi, E.; Bonaccini, C.; Gratteri, P.; Sim, L.; Gloster, T. M.; Roberts, S.; Davies, G. J.; Rose, D. R.; Goti, A. Chem.;Eur. J. 2009, 15, 1627-1636.
-
Cardona, F.; Parmeggiani1, C.; Faggi, E.; Bonaccini, C.; Gratteri, P.; Sim, L.; Gloster, T. M.; Roberts, S.; Davies, G. J.; Rose, D. R.; Goti, A. Chem.;Eur. J. 2009, 15, 1627-1636.
-
-
-
-
21
-
-
0025943456
-
-
For previous syntheses of australine see: a
-
For previous syntheses of australine see: (a) Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513-5516.
-
(1991)
Tetrahedron Lett
, vol.32
, pp. 5513-5516
-
-
Pearson, W.H.1
Hines, J.V.2
-
22
-
-
0032578178
-
-
(b) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359-7360.
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 7359-7360
-
-
White, J.D.1
Hrnciar, P.2
Yokochi, A.F.T.3
-
27
-
-
33846437463
-
-
(g) Ribes, C.; Falomir, E.; Carda, M.; Marco, J. A. Org. Lett. 2007, 9, 77-80.
-
(2007)
Org. Lett
, vol.9
, pp. 77-80
-
-
Ribes, C.1
Falomir, E.2
Carda, M.3
Marco, J.A.4
-
28
-
-
36649002237
-
-
(h) Trost, B. M.; Aponick, A.; Stanzl, B. N. Chem.;Eur. J. 2007, 13, 9547-9560.
-
(2007)
Chem.;Eur. J
, vol.13
, pp. 9547-9560
-
-
Trost, B.M.1
Aponick, A.2
Stanzl, B.N.3
-
29
-
-
0028297871
-
-
For a synthesis of australine from castanospermine see
-
(i) For a synthesis of australine from castanospermine see: Furneaux, R. H.; Gainsford,G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131-2160.
-
(1994)
Tetrahedron
, vol.50
, pp. 2131-2160
-
-
Furneaux, R.H.1
Gainsford, G.J.2
Mason, J.M.3
Tyler, P.C.4
-
30
-
-
75749085533
-
-
For previous syntheses of 3-epi-australine see: refs 14c and 14f.
-
For previous syntheses of 3-epi-australine see: refs 14c and 14f.
-
-
-
-
31
-
-
2142652135
-
-
Davis, A. S.; Pyne, S. G.; Skelton, B. W.; White, A. H. J. Org. Chem. 2004, 69, 3139-3143.
-
(2004)
J. Org. Chem
, vol.69
, pp. 3139-3143
-
-
Davis, A.S.1
Pyne, S.G.2
Skelton, B.W.3
White, A.H.4
-
37
-
-
37049076011
-
-
Casiraghi, G.; Ulgheri, F.; Spanu, P.; Rassu, G.; Pinna, L.; Gasparri, F. G.; Pelosi, F. M. G. J. Chem. Soc., Perkin Trans. I 1993, 2991-2997.
-
(1993)
J. Chem. Soc., Perkin Trans. I
, pp. 2991-2997
-
-
Casiraghi, G.1
Ulgheri, F.2
Spanu, P.3
Rassu, G.4
Pinna, L.5
Gasparri, F.G.6
Pelosi, F.M.G.7
-
38
-
-
0028296778
-
-
Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358-1364.
-
(1994)
J. Org. Chem
, vol.59
, pp. 1358-1364
-
-
Naruse, M.1
Aoyagi, S.2
Kibayashi, C.3
-
40
-
-
0035831144
-
-
Zhao, H.; Hans, S.; Chemg, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761-1767.
-
(2001)
J. Org. Chem
, vol.66
, pp. 1761-1767
-
-
Zhao, H.1
Hans, S.2
Chemg, X.3
Mootoo, D.R.4
-
41
-
-
0028855525
-
-
Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291-1294.
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 1291-1294
-
-
Zhou, W.-S.1
Xie, W.-G.2
Lu, Z.-H.3
Pan, X.-F.4
-
42
-
-
75749158288
-
-
Unfortunately we have not been able to obtain a copy of the NMR spectra of uniflorine A for comparison purposes from the original authors.1
-
1
-
-
-
-
43
-
-
33751154457
-
-
Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889.
-
(1995)
J. Org. Chem
, vol.60
, pp. 3887-3889
-
-
Yang, D.1
Wong, M.-K.2
Yip, Y.-C.3
-
44
-
-
75749114917
-
-
Crystal/refinement data have been deposited with the Cambridge Crystallographic Data Centre as CCDC 752850
-
Crystal/refinement data have been deposited with the Cambridge Crystallographic Data Centre as CCDC 752850.
-
-
-
-
46
-
-
0034731630
-
-
Ahn, J.-B.; Yun, C.-S.; Kim, H.; Ha, D.-C. J. Org. Chem. 2000, 65, 9249-9251.
-
(2000)
J. Org. Chem
, vol.65
, pp. 9249-9251
-
-
Ahn, J.-B.1
Yun, C.-S.2
Kim, H.3
Ha, D.-C.4
-
47
-
-
0037419409
-
-
Papaioannou, N.; Blank, J. T.; Miller, S. J. J. Org. Chem. 2003, 68, 2728-2734.
-
(2003)
J. Org. Chem
, vol.68
, pp. 2728-2734
-
-
Papaioannou, N.1
Blank, J.T.2
Miller, S.J.3
-
49
-
-
0032541188
-
-
Wormald, M. R.; Nash, R. J.; Hrnciar, P.; White, J. D.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1998, 9, 2549-2558.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 2549-2558
-
-
Wormald, M.R.1
Nash, R.J.2
Hrnciar, P.3
White, J.D.4
Molyneux, R.J.5
Fleet, G.W.J.6
-
50
-
-
75749127586
-
-
13CNMR chemical shifts for natural and synthetic australine see the Supporting Information in ref 14g.
-
13CNMR chemical shifts for natural and synthetic australine see the Supporting Information in ref 14g.
-
-
-
-
51
-
-
27944454053
-
-
Chikkanna, D.; Singh, O. V.; Kong, S. B.; Han, H. Tetrahedron Lett. 2005, 46, 8865-8868.
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 8865-8868
-
-
Chikkanna, D.1
Singh, O.V.2
Kong, S.B.3
Han, H.4
-
52
-
-
54049118080
-
-
For a flexible synthetic strategy for preparing several hyacinthacine alkaloids and epimers and 2,3,7-tri-epi-australine see: Donohoe, T. J.; Thomas, R. E.; Cheeseman, M. D.; Rigby, C. L.; Bhalay, G.; Linney, I. D. Org. Lett. 2008, 10, 3615-3618.
-
For a flexible synthetic strategy for preparing several hyacinthacine alkaloids and epimers and 2,3,7-tri-epi-australine see: Donohoe, T. J.; Thomas, R. E.; Cheeseman, M. D.; Rigby, C. L.; Bhalay, G.; Linney, I. D. Org. Lett. 2008, 10, 3615-3618.
-
-
-
-
53
-
-
73349116870
-
-
After submission of this manuscript an alternative synthesis of uniflorine A was published, see
-
After submission of this manuscript an alternative synthesis of uniflorine A was published, see: Parmeggiani, C.; Martella, D.; Cardona, F.; Goti, A. J. Nat. Prod. 2009, 72, 2058-2060.
-
(2009)
J. Nat. Prod
, vol.72
, pp. 2058-2060
-
-
Parmeggiani, C.1
Martella, D.2
Cardona, F.3
Goti, A.4
-
54
-
-
75749150283
-
-
3 solution unless otherwise indicated. NMR assignments are based upon COSY and HSQC, and sometimes HMBC and NOESY, NMR experiments. All IR spectra were run on neat samples.
-
3 solution unless otherwise indicated. NMR assignments are based upon COSY and HSQC, and sometimes HMBC and NOESY, NMR experiments. All IR spectra were run on neat samples.
-
-
-
|