-
1
-
-
0036910440
-
-
For general reviews on pyrrolizidine alkaloids, see: and the previous papers in this series
-
For general reviews on pyrrolizidine alkaloids, see:. Liddell J.R. Nat. Prod. Rep. 19 (2002) 773-781 and the previous papers in this series
-
(2002)
Nat. Prod. Rep.
, vol.19
, pp. 773-781
-
-
Liddell, J.R.1
-
2
-
-
17744416590
-
-
Asano N., Kuroi H., Ikeda K., Kizu H., Kameda Y., Kato A., Adachi I., Watson A.A., Nash R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 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
-
3
-
-
67650549659
-
-
For further reviews on the chemistry and biology of pyrrolizidine alkaloids, see
-
For further reviews on the chemistry and biology of pyrrolizidine alkaloids, see:
-
-
-
-
8
-
-
67650513268
-
-
For recent reviews on syntheses of this compound class
-
For recent reviews on syntheses of this compound class:
-
-
-
-
11
-
-
67650516735
-
-
For representative examples, see
-
For representative examples, see:
-
-
-
-
15
-
-
41549150619
-
-
Izquierdo I., Plaza M.T., Tamayo J.A., Yáñez V., Lo Re D., and Sánchez-Cantalejo F. Tetrahedron 64 (2008) 4613-4618
-
(2008)
Tetrahedron
, vol.64
, pp. 4613-4618
-
-
Izquierdo, I.1
Plaza, M.T.2
Tamayo, J.A.3
Yáñez, V.4
Lo Re, D.5
Sánchez-Cantalejo, F.6
-
16
-
-
67650561130
-
-
For the use of non-sugar chiral starting materials, see for example
-
For the use of non-sugar chiral starting materials, see for example:
-
-
-
-
17
-
-
41149096037
-
-
Reddy P.K., Veyron A., Koos P., Bayle A., Greene A.E., and Delair P. Org. Biomol. Chem. 6 (2008) 1170-1172
-
(2008)
Org. Biomol. Chem.
, vol.6
, pp. 1170-1172
-
-
Reddy, P.K.1
Veyron, A.2
Koos, P.3
Bayle, A.4
Greene, A.E.5
Delair, P.6
-
18
-
-
47049117544
-
-
Sengoku T., Satoh Y., Oshima M., Takahashi M., and Yoda H. Tetrahedron 64 (2008) 8052-8058
-
(2008)
Tetrahedron
, vol.64
, pp. 8052-8058
-
-
Sengoku, T.1
Satoh, Y.2
Oshima, M.3
Takahashi, M.4
Yoda, H.5
-
19
-
-
54049118080
-
-
Donohoe T.J., Thomas R.E., Cheeseman M.D., Rigby C.L., Bhalay G., and Linney I.D. Org. Lett. 10 (2008) 3615-3618
-
(2008)
Org. Lett.
, vol.10
, pp. 3615-3618
-
-
Donohoe, T.J.1
Thomas, R.E.2
Cheeseman, M.D.3
Rigby, C.L.4
Bhalay, G.5
Linney, I.D.6
-
21
-
-
67650519028
-
-
For previous syntheses of hyacinthacine A2 (2) see:
-
For previous syntheses of hyacinthacine A2 (2) see:
-
-
-
-
23
-
-
0037430434
-
-
Cardona F., Faggi E., Liguori F., Cacciarini M., and Goti A. Tetrahedron Lett. 44 (2003) 2315-2318
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 2315-2318
-
-
Cardona, F.1
Faggi, E.2
Liguori, F.3
Cacciarini, M.4
Goti, A.5
-
29
-
-
67649398994
-
-
Ribes C., Falomir E., Murga J., Carda M., and Marco J.A. Org. Biomol. Chem. 7 (2009) 1355-1360
-
(2009)
Org. Biomol. Chem.
, vol.7
, pp. 1355-1360
-
-
Ribes, C.1
Falomir, E.2
Murga, J.3
Carda, M.4
Marco, J.A.5
-
30
-
-
53049084856
-
-
For a recent synthesis of radicamine B, a further pyrrolidine alkaloid which also contains the structural fragment I, see:
-
For a recent synthesis of radicamine B, a further pyrrolidine alkaloid which also contains the structural fragment I, see:. Ribes C., Falomir E., Carda M., and Marco J.A. J. Org. Chem. 73 (2008) 7779-7782
-
(2008)
J. Org. Chem.
, vol.73
, pp. 7779-7782
-
-
Ribes, C.1
Falomir, E.2
Carda, M.3
Marco, J.A.4
-
32
-
-
33846437463
-
-
In our recent synthesis of the pyrrolizidine alkaloid australine, all three C-N bonds of the heterobicyclic system were formed in a one-pot procedure:
-
In our recent synthesis of the pyrrolizidine alkaloid australine, all three C-N bonds of the heterobicyclic system were formed in a one-pot procedure:. Ribes C., Falomir E., Carda M., and Marco J.A. Org. Lett. 9 (2007) 77-80
-
(2007)
Org. Lett.
, vol.9
, pp. 77-80
-
-
Ribes, C.1
Falomir, E.2
Carda, M.3
Marco, J.A.4
-
33
-
-
0001659326
-
-
Trost B.M., Fleming I., and Winterfeldt E. (Eds), Pergamon, Oxford
-
Tsuji J. In: Trost B.M., Fleming I., and Winterfeldt E. (Eds). Comprehensive Organic Synthesis Vol. 7 (1993), Pergamon, Oxford 449-468
-
(1993)
Comprehensive Organic Synthesis
, vol.7
, pp. 449-468
-
-
Tsuji, J.1
-
36
-
-
67650566306
-
-
note
-
For previous syntheses of 5-epi-3, see Refs. 5c and d.
-
-
-
-
38
-
-
67650531073
-
-
note
-
The compound reported in Ref. 8 (numbered 4 there) is a dehydro derivative of 19 showing an additional C{double bond, long}C bond in the side chain. In the reaction conditions described by the authors, this compound was assumed to undergo hydrogenation to 19 (numbered 5) in a neutral medium as the first step. The acid was added to the reaction medium only after this initial step had taken place.
-
-
-
-
39
-
-
37049070346
-
-
Lathbury D.C., Shaw R.W., Bates P.A., Hursthouse M.B., and Gallagher T. J. Chem. Soc., Perkin Trans. 1 (1989) 2415-2424
-
(1989)
J. Chem. Soc., Perkin Trans. 1
, pp. 2415-2424
-
-
Lathbury, D.C.1
Shaw, R.W.2
Bates, P.A.3
Hursthouse, M.B.4
Gallagher, T.5
-
43
-
-
0034608470
-
-
Takahata H., Takahashi S., Azer N., Eldefrawi A.T., and Eldefrawi M.E. Bioorg. Med. Chem. Lett. 10 (2000) 1293-1295
-
(2000)
Bioorg. Med. Chem. Lett.
, vol.10
, pp. 1293-1295
-
-
Takahata, H.1
Takahashi, S.2
Azer, N.3
Eldefrawi, A.T.4
Eldefrawi, M.E.5
-
47
-
-
67650522854
-
-
note
-
7d in the range 3-11% from commercial precursors. For 3 and 5-epi-3, the sequence contains 15 steps along the respective synthetic routes 5→16→3 and 5→16→5-epi-3. The overall yields were ca. 14% and 21%, respectively.
-
-
-
|