-
1
-
-
0036360649
-
-
For reviews on the subject, see
-
a) For reviews on the subject, see: J. Hartung, T. Gottwald, K. Spehar, Synthesis 2002, 1469-1498;
-
(2002)
Synthesis
, pp. 1469-1498
-
-
Hartung, J.1
Gottwald, T.2
Spehar, K.3
-
4
-
-
0000124573
-
-
Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
-
d) W. Zhang in Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, vol. 2, pp. 234-245;
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 234-245
-
-
Zhang, W.1
-
5
-
-
0000213430
-
-
Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
-
e) E. Suárez, M. S. Rodríguez in Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, vol. 2, pp. 440-454;
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 440-454
-
-
Suárez, E.1
Rodríguez, M.S.2
-
8
-
-
0034246704
-
-
h) L. Yet, Chem. Rev. 2000, 100, 2963-3007;
-
(2000)
Chem. Rev
, vol.100
, pp. 2963-3007
-
-
Yet, L.1
-
11
-
-
0001226680
-
-
Ed, R. A. Abramovitch, Plenum Press, New York
-
k) P. Brun, B. Waegell in Reactive Intermediates (Ed.: R. A. Abramovitch), Plenum Press, New York, 1983, vol. 3, pp. 367-426;
-
(1983)
Reactive Intermediates
, vol.3
, pp. 367-426
-
-
Brun, P.1
Waegell, B.2
-
12
-
-
0033607760
-
-
See also:, and references cited therein
-
l) See also: S. Wilsey, P. Dowd, K. N. Houk, J. Org. Chem. 1999, 64, 8801-8811 and references cited therein.
-
(1999)
J. Org. Chem
, vol.64
, pp. 8801-8811
-
-
Wilsey, S.1
Dowd, P.2
Houk, K.N.3
-
13
-
-
33744820012
-
-
For some recent examples, see
-
a) For some recent examples, see: S. Chiba, M. Kitamura, K. Narasaka, J. Am. Chem. Soc. 2006, 128, 6931-6937;
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 6931-6937
-
-
Chiba, S.1
Kitamura, M.2
Narasaka, K.3
-
15
-
-
12344321513
-
-
c) K. Takasu, S. Nagao, M. Ihara, Tetrahedron Lett. 2005, 46, 1005-1008;
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 1005-1008
-
-
Takasu, K.1
Nagao, S.2
Ihara, M.3
-
16
-
-
21844462579
-
-
d) C. R. Alonso-Cruz, E.I. León, F. J. Ortiz-López, M. S. Rodríguez, E. Suárez, Tetrahedron Lett. 2005, 46, 5265-5268;
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 5265-5268
-
-
Alonso-Cruz, C.R.1
León, E.I.2
Ortiz-López, F.J.3
Rodríguez, M.S.4
Suárez, E.5
-
17
-
-
23444431603
-
-
e) C. L. L. Chai, J. A. Elix, P. B. Huleatt, Tetrahedron 2005, 61, 8722-8739;
-
(2005)
Tetrahedron
, vol.61
, pp. 8722-8739
-
-
Chai, C.L.L.1
Elix, J.A.2
Huleatt, P.B.3
-
18
-
-
18144379853
-
-
f) C. De Dobbeleer, A. Ates, J. C. Vanherk, I. E. Marko, Tetrahedron Lett. 2005, 46, 3889-3893;
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 3889-3893
-
-
De Dobbeleer, C.1
Ates, A.2
Vanherk, J.C.3
Marko, I.E.4
-
19
-
-
23644452967
-
-
g) M. Bietti, G. Gente, M. Salamone, J. Org. Chem. 2005, 70, 6820-6826;
-
(2005)
J. Org. Chem
, vol.70
, pp. 6820-6826
-
-
Bietti, M.1
Gente, G.2
Salamone, M.3
-
20
-
-
24944507270
-
-
h) T. Akindele, S. P. Marsden, J. G. Cumming, Tetrahedron Lett. 2005, 46, 7235-7238;
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 7235-7238
-
-
Akindele, T.1
Marsden, S.P.2
Cumming, J.G.3
-
21
-
-
25144457996
-
-
j
-
i) H. Rudler, B. Denise, Y. Xu, A. Parlier, J. Vaissermann, Eur. J. Org. Chem. 2005, 3724-3744; j
-
(2005)
Eur. J. Org. Chem
, pp. 3724-3744
-
-
Rudler, H.1
Denise, B.2
Xu, Y.3
Parlier, A.4
Vaissermann, J.5
-
22
-
-
20544454057
-
-
j) Z. Ferjancic, R. Matovic, Z. Cekovic, J. P. Snyder, R. N. Saicic, Tetrahedron Lett. 2005, 46, 5049-5052;
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 5049-5052
-
-
Ferjancic, Z.1
Matovic, R.2
Cekovic, Z.3
Snyder, J.P.4
Saicic, R.N.5
-
23
-
-
9344260281
-
-
k) R. Hernández, E. I. de León, C. Riesco-Fagundo, E. Suárez, J. Org. Chem. 2004, 69, 8437-8444;
-
(2004)
J. Org. Chem
, vol.69
, pp. 8437-8444
-
-
Hernández, R.1
de León, E.I.2
Riesco-Fagundo, C.3
Suárez, E.4
-
24
-
-
0842326655
-
-
l) K.-i. Fuhsuku, M. Tomita, T. Sugai, Tetrahedron Lett. 2004, 45, 1763-1769;
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 1763-1769
-
-
Fuhsuku, K.-I.1
Tomita, M.2
Sugai, T.3
-
25
-
-
1842420404
-
-
m) M. A. Iglesias-Arteaga, E. Juaristi, F. J. Gonzalez, Tetrahedron 2004, 60, 3605-3610;
-
(2004)
Tetrahedron
, vol.60
, pp. 3605-3610
-
-
Iglesias-Arteaga, M.A.1
Juaristi, E.2
Gonzalez, F.J.3
-
26
-
-
3543007143
-
-
n) C. S. A. Antunes, M. Bietti, O. Lanzalunga, M. Salamone, J. Org. Chem. 2004, 69, 5281-5289;
-
(2004)
J. Org. Chem
, vol.69
, pp. 5281-5289
-
-
Antunes, C.S.A.1
Bietti, M.2
Lanzalunga, O.3
Salamone, M.4
-
30
-
-
0037424549
-
-
r) M. A. Iglesias-Arteaga, E. Castellanos, E. Juaristi, Tetrahedron: Asymmetry 2003, 14, 577-580;
-
(2003)
Tetrahedron: Asymmetry
, vol.14
, pp. 577-580
-
-
Iglesias-Arteaga, M.A.1
Castellanos, E.2
Juaristi, E.3
-
33
-
-
0038208388
-
-
For other interesting examples, see:, and references cited therein
-
u) For other interesting examples, see: A. Boto, D. Hernández, R. Hernández, E. Suárez, J. Org. Chem. 2003, 68, 5310-5319 and references cited therein.
-
(2003)
J. Org. Chem
, vol.68
, pp. 5310-5319
-
-
Boto, A.1
Hernández, D.2
Hernández, R.3
Suárez, E.4
-
34
-
-
10844229059
-
-
a) T. Yoshimitsu, S. Sasaki, Y. Arano, H. Nagaoka, J. Org. Chem. 2004, 69, 9262-9268;
-
(2004)
J. Org. Chem
, vol.69
, pp. 9262-9268
-
-
Yoshimitsu, T.1
Sasaki, S.2
Arano, Y.3
Nagaoka, H.4
-
35
-
-
0034676525
-
-
b) T. Yoshimitsu, S. Yanagisawa, H. Nagaoka, Org. Lett. 2000, 2, 3751-3754;
-
(2000)
Org. Lett
, vol.2
, pp. 3751-3754
-
-
Yoshimitsu, T.1
Yanagisawa, S.2
Nagaoka, H.3
-
37
-
-
0037047546
-
-
d) A. F. Barrero, J. E. Oltra, M. Alvarez, A. Rosales, J. Org. Chem. 2002, 67, 5461-5469;
-
(2002)
J. Org. Chem
, vol.67
, pp. 5461-5469
-
-
Barrero, A.F.1
Oltra, J.E.2
Alvarez, M.3
Rosales, A.4
-
38
-
-
0027994894
-
-
e) R. Hernández, S. M. Velázquez, E. Suárez, M. S. Rodríguez, J. Org. Chem. 1994, 59, 6395-6403;
-
(1994)
J. Org. Chem
, vol.59
, pp. 6395-6403
-
-
Hernández, R.1
Velázquez, S.M.2
Suárez, E.3
Rodríguez, M.S.4
-
39
-
-
0344382057
-
-
f) P. de Armas, F. García-Tellado, J. J. Marrero-Tellado, J. Robles, Tetrahedron Lett. 1990, 39, 131-134.
-
(1990)
Tetrahedron Lett
, vol.39
, pp. 131-134
-
-
de Armas, P.1
García-Tellado, F.2
Marrero-Tellado, J.J.3
Robles, J.4
-
40
-
-
0141570904
-
-
a) Z. Cekovic, Tetrahedron 2003, 59, 8073-8090;
-
(2003)
Tetrahedron
, vol.59
, pp. 8073-8090
-
-
Cekovic, Z.1
-
41
-
-
0001238367
-
-
Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
-
b) L. Feray, N. Kuznetsov, P. Renaud in Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, vol. 2, pp. 246-278;
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 246-278
-
-
Feray, L.1
Kuznetsov, N.2
Renaud, P.3
-
42
-
-
57249084541
-
-
c) J. Robertson, J. Pillai, R. K. Lush, Chem. Soc. Rev. 2001, 30, 94-103;
-
(2001)
Chem. Soc. Rev
, vol.30
, pp. 94-103
-
-
Robertson, J.1
Pillai, J.2
Lush, R.K.3
-
43
-
-
0029036335
-
-
and references cited therein
-
d) G. Majetich, K. Wheless, Tetrahedron 1995, 51, 7095-7129 and references cited therein.
-
(1995)
Tetrahedron
, vol.51
, pp. 7095-7129
-
-
Majetich, G.1
Wheless, K.2
-
46
-
-
0038317136
-
-
Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
-
c) J. Hartung in Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, vol. 2, pp. 427-439.
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 427-439
-
-
Hartung, J.1
-
47
-
-
33846533863
-
-
We have recently reported (ref.[2t, that the primary alkoxy radicals derived from carbohydrates in the furanose form gave a mixture of fragmentation and intramolecular hydrogen abstraction IHA, By controlling the reaction conditions, the stereochemistry of the substituents and the protecting groups, the β-fragmentation was made to predominate over the side reactions. In contrast, the substrates described in this article gave scission as the sole reaction
-
[2t]) that the primary alkoxy radicals derived from carbohydrates in the furanose form gave a mixture of fragmentation and intramolecular hydrogen abstraction (IHA). By controlling the reaction conditions, the stereochemistry of the substituents and the protecting groups, the β-fragmentation was made to predominate over the side reactions. In contrast, the substrates described in this article gave scission as the sole reaction.
-
-
-
-
48
-
-
1642578949
-
-
For a preliminary communication of this work, see
-
For a preliminary communication of this work, see: A. Boto, R. Hernández, A. Montoya, E. Suárez, Tetrahedron Lett. 2004, 45, 1559-1563.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 1559-1563
-
-
Boto, A.1
Hernández, R.2
Montoya, A.3
Suárez, E.4
-
49
-
-
14944348259
-
-
For a discussion on the mechanism of the oxidation step, see
-
a) For a discussion on the mechanism of the oxidation step, see: A. Boto, R. Hernández, Y. Leon, J. R. Murguía, A. Rodríguez-Afonso, Eur. J. Org. Chem. 2005, 673-682;
-
(2005)
Eur. J. Org. Chem
, pp. 673-682
-
-
Boto, A.1
Hernández, R.2
Leon, Y.3
Murguía, J.R.4
Rodríguez-Afonso, A.5
-
50
-
-
26444523953
-
-
For related works, see
-
b) For related works, see: A. Boto, J. A. Gallardo, R. Hernández, C. J. Saavedra, Tetrahedron Lett. 2005, 46, 7807-7811;
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 7807-7811
-
-
Boto, A.1
Gallardo, J.A.2
Hernández, R.3
Saavedra, C.J.4
-
51
-
-
23944472481
-
-
c) A. Boto, Y. De León, J. A. Gallardo, R. Hernández, Eur. J. Org. Chem. 2005, 3461-3468;
-
(2005)
Eur. J. Org. Chem
, pp. 3461-3468
-
-
Boto, A.1
De León, Y.2
Gallardo, J.A.3
Hernández, R.4
-
52
-
-
0037064474
-
-
A. Boto, R. Hernández, A. Montoya, E. Suárez, Tetrahedron Lett. 2002, 43, 8269-8272;
-
d) A. Boto, R. Hernández, A. Montoya, E. Suárez, Tetrahedron Lett. 2002, 43, 8269-8272;
-
-
-
-
53
-
-
0035900387
-
-
e) A. Boto, R. Hernández, Y. León, E. Suárez, J. Org. Chem. 2001, 65, 7796-7803;
-
(2001)
J. Org. Chem
, vol.65
, pp. 7796-7803
-
-
Boto, A.1
Hernández, R.2
León, Y.3
Suárez, E.4
-
54
-
-
0343167391
-
-
f) A. Boto, R. Hernández, E. Suárez, J. Org. Chem. 2000, 64, 4930-4937.
-
(2000)
J. Org. Chem
, vol.64
, pp. 4930-4937
-
-
Boto, A.1
Hernández, R.2
Suárez, E.3
-
55
-
-
1842430777
-
-
For recent reviews on acyliminium ions, see
-
a) For recent reviews on acyliminium ions, see: B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431-1628;
-
(2004)
Chem. Rev
, vol.104
, pp. 1431-1628
-
-
Maryanoff, B.E.1
Zhang, H.-C.2
Cohen, J.H.3
Turchi, I.J.4
Maryanoff, C.A.5
-
56
-
-
2942574530
-
-
b) J. Royer, M. Bonin, L. Micouin, Chem. Rev. 2004, 104, 2311-2352;
-
(2004)
Chem. Rev
, vol.104
, pp. 2311-2352
-
-
Royer, J.1
Bonin, M.2
Micouin, L.3
-
57
-
-
0000308759
-
-
See also
-
c) See also: P. D. Bailey, A. N. Boa, J. Clayson, Contemp. Org. Synth. 1995, 2, 173-187;
-
(1995)
Contemp. Org. Synth
, vol.2
, pp. 173-187
-
-
Bailey, P.D.1
Boa, A.N.2
Clayson, J.3
-
58
-
-
0001673091
-
-
Pergamon Press, Oxford
-
d) W. N. Speckamp, H. Hiemstra in Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, vol. 2, pp. 1047-1082.
-
(1991)
Comprehensive Organic Synthesis
, vol.2
, pp. 1047-1082
-
-
Speckamp, W.N.1
Hiemstra, H.2
-
59
-
-
0141925985
-
-
F. X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693-3712 and references cited therein;
-
a) F. X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693-3712 and references cited therein;
-
-
-
-
61
-
-
0033714636
-
-
For a review on the subject, see
-
c) For a review on the subject, see: F. Fache, E. Schultz, M. L. Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231;
-
(2000)
Chem. Rev
, vol.100
, pp. 2159-2231
-
-
Fache, F.1
Schultz, E.2
Tommasino, M.L.3
Lemaire, M.4
-
62
-
-
0003780442
-
-
Eds, P. G. Sammes, J. B. Taylor, Pergamon Press, Oxford, vols, and 3
-
d) Comprehensive Medicinal Chemistry (Eds.: P. G. Sammes, J. B. Taylor), Pergamon Press, Oxford, 1990, vols. 2 and 3.
-
(1990)
Comprehensive Medicinal Chemistry
, vol.2
-
-
-
63
-
-
0026533264
-
-
a) J. A. Seijas, M. P. Vázquez-Tato, L. Castedo, R. J. Estévez, M. G. Ónega, M. Ruiz, Tetrahedron 1992, 48, 1637-1642;
-
(1992)
Tetrahedron
, vol.48
, pp. 1637-1642
-
-
Seijas, J.A.1
Vázquez-Tato, M.P.2
Castedo, L.3
Estévez, R.J.4
Ónega, M.G.5
Ruiz, M.6
-
66
-
-
37049067325
-
-
a) T. Sato, Y. Kugo, E. Nakaumi, H. Ishibashi, M. Ikeda, J. Chem. Soc., Perkin Trans. 1 1995, 1801-1810;
-
(1995)
J. Chem. Soc., Perkin Trans. 1
, pp. 1801-1810
-
-
Sato, T.1
Kugo, Y.2
Nakaumi, E.3
Ishibashi, H.4
Ikeda, M.5
-
67
-
-
0030885245
-
-
b) H. Takahata, M. Kubota, T. Momose, Tetrahedron: Asymmetry 1997, 8, 2801-2810.
-
(1997)
Tetrahedron: Asymmetry
, vol.8
, pp. 2801-2810
-
-
Takahata, H.1
Kubota, M.2
Momose, T.3
-
68
-
-
0343415173
-
-
a) A. Boto, R. Hernández, E. Suárez, Tetrahedron Lett. 2000, 41, 2899-2902;
-
(2000)
Tetrahedron Lett
, vol.41
, pp. 2899-2902
-
-
Boto, A.1
Hernández, R.2
Suárez, E.3
-
69
-
-
0037424287
-
-
See also
-
b) See also: M. Amat, N. Llor, J. Hidalgo, C. Escolano, J. Bosch, J. Org. Chem. 2003, 68, 1919-1928;
-
(2003)
J. Org. Chem
, vol.68
, pp. 1919-1928
-
-
Amat, M.1
Llor, N.2
Hidalgo, J.3
Escolano, C.4
Bosch, J.5
-
70
-
-
0034719260
-
-
and references cited therein
-
c) T. J. Wilkinson, N. W. Stehle, P. Beak, Org. Lett. 2000, 2, 155-158 and references cited therein.
-
(2000)
Org. Lett
, vol.2
, pp. 155-158
-
-
Wilkinson, T.J.1
Stehle, N.W.2
Beak, P.3
-
71
-
-
7444224237
-
-
a) C. Pousset, R. Callens, M. Haddad, M. Larcheveque, Tetrahedron: Asymmetry 2004, 15, 3407-3412;
-
(2004)
Tetrahedron: Asymmetry
, vol.15
, pp. 3407-3412
-
-
Pousset, C.1
Callens, R.2
Haddad, M.3
Larcheveque, M.4
-
72
-
-
0026640191
-
-
b) T. Shono, J. Terauchi, K. Kitayama, Y.-i. Takeshima, Y. Matsumura, Tetrahedron 1992, 48, 8253-8262.
-
(1992)
Tetrahedron
, vol.48
, pp. 8253-8262
-
-
Shono, T.1
Terauchi, J.2
Kitayama, K.3
Takeshima, Y.-I.4
Matsumura, Y.5
-
73
-
-
33845374499
-
-
T. Shono, Y. Matsumura, K. Tsubata, K. Uchida, J. Org. Chem. 1986, 51, 2590-2592.
-
(1986)
J. Org. Chem
, vol.51
, pp. 2590-2592
-
-
Shono, T.1
Matsumura, Y.2
Tsubata, K.3
Uchida, K.4
-
76
-
-
37049079163
-
-
c) D. R. Adams, W. Carruthers, M. J. Williams, P. J. Crowley, J. Chem. Soc., Perkin Trans. 1 1989, 1507-1513.
-
(1989)
J. Chem. Soc., Perkin Trans. 1
, pp. 1507-1513
-
-
Adams, D.R.1
Carruthers, W.2
Williams, M.J.3
Crowley, P.J.4
-
77
-
-
0032897645
-
-
S. Brocherieux-Lanoy, H. Dhimane, C. Vanucci-Bacque, G. Lhommet, Synlett 1999, 405-408.
-
(1999)
Synlett
, pp. 405-408
-
-
Brocherieux-Lanoy, S.1
Dhimane, H.2
Vanucci-Bacque, C.3
Lhommet, G.4
-
78
-
-
26844582966
-
-
For serial reviews on indolizidine and quinolizidine alkaloids, see: J. P. Michael, Nat. Prod. Rep. 2005, 22, 603-626 and references cited therein;
-
a) For serial reviews on indolizidine and quinolizidine alkaloids, see: J. P. Michael, Nat. Prod. Rep. 2005, 22, 603-626 and references cited therein;
-
-
-
-
79
-
-
0034607947
-
-
b) N. Asano, R. J. Nash, R. J. Molyneux, G. W. J. Fleet, Tetrahedron: Asymmetry 2000, 11, 1645-1680;
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 1645-1680
-
-
Asano, N.1
Nash, R.J.2
Molyneux, R.J.3
Fleet, G.W.J.4
-
80
-
-
0000584109
-
Alkaloid Glycosidase Inhibitors
-
Eds, D. H. R. Barton, K. Nakanishi, O. Meth-Cohn, Elsevier, Oxford, ch. 7;
-
c) A. D. Elbein, R. J. Molyneux, "Alkaloid Glycosidase Inhibitors" in Comprehensive Natural Products Chemistry (Eds.: D. H. R. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Oxford, 1999, vol. 3, ch. 7;
-
(1999)
Comprehensive Natural Products Chemistry
, vol.3
-
-
Elbein, A.D.1
Molyneux, R.J.2
-
82
-
-
0029870160
-
-
S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264.
-
(1996)
Tetrahedron
, vol.52
, pp. 7251-7264
-
-
Martin, S.F.1
Chen, H.-J.2
Courtney, A.K.3
Liao, Y.4
Pätzel, M.5
Ramser, M.N.6
Wagman, A.S.7
-
83
-
-
1442360753
-
-
R. H. Grubbs Ed, Wiley-VCH, Weinheim
-
R. H. Grubbs (Ed.), Handbook of Metathesis, Wiley-VCH, Weinheim, 2003.
-
(2003)
Handbook of Metathesis
-
-
-
84
-
-
0036910440
-
-
For serial reviews on pyrrolizidine alkaloids, see: J. R. Lidell, Nat. Prod. Rep. 2002, 19, 773-781 and references cited therein;
-
a) For serial reviews on pyrrolizidine alkaloids, see: J. R. Lidell, Nat. Prod. Rep. 2002, 19, 773-781 and references cited therein;
-
-
-
-
85
-
-
0004052642
-
-
For other reviews and books, see: A. F. M. Rizk Ed, CRC Press, Boston
-
b) For other reviews and books, see: A. F. M. Rizk (Ed.), Naturally Occurring Pyrrolizidine Alkaloids, CRC Press, Boston, 1991;
-
(1991)
Naturally Occurring Pyrrolizidine Alkaloids
-
-
-
86
-
-
0000724877
-
-
Ed, S. W. Pelletier, Elsevier, Oxford, ch. 4;
-
c) T. Hartmann, L. Witte in Alkaloids: Chemical and Biological Perspectives (Ed.: S. W. Pelletier), Elsevier, Oxford, 1995, vol. 9, ch. 4;
-
(1995)
Alkaloids: Chemical and Biological Perspectives
, vol.9
-
-
Hartmann, T.1
Witte, L.2
-
88
-
-
26844514473
-
-
For recent articles, see
-
e) For recent articles, see: C. Roche, K. Kadleciková, A. Veyron, P. Delair, C. Philouze, A. E. Greene, J. Org. Chem. 2005, 70, 8352-8363;
-
(2005)
J. Org. Chem
, vol.70
, pp. 8352-8363
-
-
Roche, C.1
Kadleciková, K.2
Veyron, A.3
Delair, P.4
Philouze, C.5
Greene, A.E.6
-
89
-
-
0037450388
-
-
and references cited therein
-
f) H. Yoda, T. Egawa, K. Takabe, Tetrahedron Lett. 2003, 44, 1643-1646 and references cited therein.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 1643-1646
-
-
Yoda, H.1
Egawa, T.2
Takabe, K.3
-
91
-
-
0009929120
-
Plant Chemical Ecology
-
Eds, D. H. R. Barton, K. Nakanishi, O. Meth-Cohn, Elsevier, Oxford, ch. 3;
-
b) J. B. Harborne, "Plant Chemical Ecology" in Comprehensive Natural Products Chemistry (Eds.: D. H. R. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Oxford, 1999, vol. 8, ch. 3;
-
(1999)
Comprehensive Natural Products Chemistry
, vol.8
-
-
Harborne, J.B.1
-
92
-
-
33846548792
-
-
E. D. Morgan, I. D. Wilson, Insect Hormones and Insect Chemical Ecology in Comprehensive Natural Products Chemistry (Eds.: D. H., R. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Oxford, 1999, 8, ch. 3;
-
c) E. D. Morgan, I. D. Wilson, "Insect Hormones and Insect Chemical Ecology" in Comprehensive Natural Products Chemistry (Eds.: D. H., R. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Oxford, 1999, vol. 8, ch. 3;
-
-
-
-
93
-
-
0042656793
-
-
d) P. Laurent, J.-C. Braekman, D. Daloze, J. Pasteels, Eur. J. Org. Chem. 2003, 2733-2743.
-
(2003)
Eur. J. Org. Chem
, pp. 2733-2743
-
-
Laurent, P.1
Braekman, J.-C.2
Daloze, D.3
Pasteels, J.4
-
94
-
-
33646547234
-
-
Alexines: a I. Izquierdo, M. T. Plaza, J. A. Tamayo, M. Rodríguez, A. Martos, Tetrahedron 2006, 62, 6006-6011;
-
Alexines: a) I. Izquierdo, M. T. Plaza, J. A. Tamayo, M. Rodríguez, A. Martos, Tetrahedron 2006, 62, 6006-6011;
-
-
-
-
95
-
-
33644536076
-
-
b) S. Cicchi, M. Marradi, P. Vogel, A. Goti, J. Org. Chem. 2006, 71, 1614-1619;
-
(2006)
J. Org. Chem
, vol.71
, pp. 1614-1619
-
-
Cicchi, S.1
Marradi, M.2
Vogel, P.3
Goti, A.4
-
96
-
-
27944454053
-
-
c) D. Chikkanna, O. V. Singh, S. B. Kong, H. Han, 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
-
97
-
-
0035936801
-
-
d) B. Alcaide, P. Almendros, J. M. Alonso, M. F. Aly, J. Org. Chem. 2001, 66, 1351-1358;
-
(2001)
J. Org. Chem
, vol.66
, pp. 1351-1358
-
-
Alcaide, B.1
Almendros, P.2
Alonso, J.M.3
Aly, M.F.4
-
99
-
-
0032578178
-
-
f) J. D. White, P. Hrnciar, A. F. T. Yokochi, 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
-
100
-
-
0008697109
-
-
M. Sadakane, R. Vahle, K. Schierle, D. Kolter, E. Steckhan, Synlett 1997, 95-96.
-
(1997)
Synlett
, pp. 95-96
-
-
Sadakane, M.1
Vahle, R.2
Schierle, K.3
Kolter, D.4
Steckhan, E.5
-
101
-
-
33846538187
-
1′,2 = 8.8 Hz). For the major diastereomer
-
1′,2 2 = 9.3 Hz;
-
, vol.1
, Issue.2
, pp. 2
-
-
Minor diastereomer1
-
102
-
-
32644450425
-
-
b) H. Danielec, J. Klügge, B. Schlummer, T. Bach, Synthesis 2006, 551-556;
-
(2006)
Synthesis
, pp. 551-556
-
-
Danielec, H.1
Klügge, J.2
Schlummer, B.3
Bach, T.4
-
104
-
-
0003086615
-
-
erythro, see: J.-L. Bougeois, L. Stella, J.-M. Surzur, Tetrahedron Lett. 1981, 22, 61-64.
-
erythro, see: J.-L. Bougeois, L. Stella, J.-M. Surzur, Tetrahedron Lett. 1981, 22, 61-64.
-
-
-
-
105
-
-
33846478083
-
-
Since both the old and the new batches were purchased from the same company, the different reaction results suggested that the old reagent isomerized prior to use. The isomerization of disubstituted olefins to trisubstituted alkenes is favored on thermodynamic grounds, and small amounts of acid can catalyze the process. Since chlorinated reagents release HCl with time, the isomerization could easily take place. See also: Shell Devel. Co. Patent US2042223 (1934);
-
a) Since both the old and the new batches were purchased from the same company, the different reaction results suggested that the old reagent isomerized prior to use. The isomerization of disubstituted olefins to trisubstituted alkenes is favored on thermodynamic grounds, and small amounts of acid can catalyze the process. Since chlorinated reagents release HCl with time, the isomerization could easily take place. See also: Shell Devel. Co. Patent US2042223 (1934);
-
-
-
-
106
-
-
33846544002
-
-
For related isomerizations, see: Patent US 2097154
-
b) For related isomerizations, see: Shell Devel. Co. Patent US 2097154 (1933);
-
(1933)
-
-
Shell Devel, C.1
-
108
-
-
0024584348
-
-
Sedamine analogues: P.-J. Tirel, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 1947-1950;
-
a) Sedamine analogues: P.-J. Tirel, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 1947-1950;
-
-
-
-
109
-
-
22044440895
-
-
See also
-
b) See also: D. Passarella, A. Barilli, F. Belinghieri, P. Fassi, S. Riva, A. Sacchetti, A. Silvani, B. Danieli, Tetrahedron: Asymmetry 2005, 16, 2225-2230;
-
(2005)
Tetrahedron: Asymmetry
, vol.16
, pp. 2225-2230
-
-
Passarella, D.1
Barilli, A.2
Belinghieri, F.3
Fassi, P.4
Riva, S.5
Sacchetti, A.6
Silvani, A.7
Danieli, B.8
-
110
-
-
0037023406
-
-
c) J. Cossy, C. Willis, V. Bellosta, S. BouzBouz, J. Org. Chem. 2002, 67, 1982-1992.
-
(2002)
J. Org. Chem
, vol.67
, pp. 1982-1992
-
-
Cossy, J.1
Willis, C.2
Bellosta, V.3
BouzBouz, S.4
-
111
-
-
0030066006
-
-
a) S. Louwrier, A. Tuynman, H. Hiemstra, Tetrahedron 1996, 52, 2629-2646;
-
(1996)
Tetrahedron
, vol.52
, pp. 2629-2646
-
-
Louwrier, S.1
Tuynman, A.2
Hiemstra, H.3
-
112
-
-
0001404364
-
-
b) T. Shono, Y. Matsumura, K. Uchida, K. Tsubata, A. Makino, J. Org. Chem. 1984, 49, 300-304.
-
(1984)
J. Org. Chem
, vol.49
, pp. 300-304
-
-
Shono, T.1
Matsumura, Y.2
Uchida, K.3
Tsubata, K.4
Makino, A.5
-
114
-
-
0035479668
-
-
For other articles on the subject, see
-
b) For other articles on the subject, see: M. C. F. de Oliveira, L. S. Santos, R. A. Pilli, Tetrahedron Lett. 2001, 42, 6995-6997;
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 6995-6997
-
-
de Oliveira, M.C.F.1
Santos, L.S.2
Pilli, R.A.3
-
116
-
-
0033521168
-
-
d) M. Pichon, R. Hocquemiller, B. Figadère, Tetrahedron Lett. 1999, 40, 8567-8570;
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 8567-8570
-
-
Pichon, M.1
Hocquemiller, R.2
Figadère, B.3
-
117
-
-
0035897085
-
-
For reviews on the subject, see
-
e) For reviews on the subject, see: S. K. Bur, S. F. Martin, Tetrahedron 2001, 57, 3221-3242;
-
(2001)
Tetrahedron
, vol.57
, pp. 3221-3242
-
-
Bur, S.K.1
Martin, S.F.2
-
118
-
-
0034421824
-
-
f) G. Rassu, F. Zanardi, L. Battistini, G. Casiraghi, Chem. Soc. Rev. 2000, 29, 109-118.
-
(2000)
Chem. Soc. Rev
, vol.29
, pp. 109-118
-
-
Rassu, G.1
Zanardi, F.2
Battistini, L.3
Casiraghi, G.4
-
119
-
-
0034797193
-
-
H. Takayama, T. Ichikawa, M. Kitajima, M. G. Nonato, N. Aimi, J. Nat. Prod. 2001, 64, 1224-1225.
-
(2001)
J. Nat. Prod
, vol.64
, pp. 1224-1225
-
-
Takayama, H.1
Ichikawa, T.2
Kitajima, M.3
Nonato, M.G.4
Aimi, N.5
-
120
-
-
0037459751
-
-
a) K. H. Lee, J. S. Chun, C. S. Pak, J. Org. Chem. 2003, 68, 2471-2474;
-
(2003)
J. Org. Chem
, vol.68
, pp. 2471-2474
-
-
Lee, K.H.1
Chun, J.S.2
Pak, C.S.3
-
121
-
-
0036794015
-
-
b) A. Sudau, W. Münch, J.-W. Bats, U. Nubbemeyer, Eur. J. Org. Chem. 2002, 3304-3314;
-
(2002)
Eur. J. Org. Chem
, pp. 3304-3314
-
-
Sudau, A.1
Münch, W.2
Bats, J.-W.3
Nubbemeyer, U.4
-
122
-
-
0034614462
-
-
For related examples, see
-
c) For related examples, see: M. Lombardo, C. Trombini, Tetrahedron 2000, 56, 323-326;
-
(2000)
Tetrahedron
, vol.56
, pp. 323-326
-
-
Lombardo, M.1
Trombini, C.2
-
123
-
-
0032794901
-
-
d) G. Rassu, P. Carta, L. Pinna, L. Battistini, F. Zanardi, D. Acquotti, G. Casiraghi, Eur. J. Org. Chem. 1999, 1395-1400;
-
(1999)
Eur. J. Org. Chem
, pp. 1395-1400
-
-
Rassu, G.1
Carta, P.2
Pinna, L.3
Battistini, L.4
Zanardi, F.5
Acquotti, D.6
Casiraghi, G.7
-
125
-
-
0001028588
-
-
For a related strategy, see
-
For a related strategy, see: N. Ikota, Heterocycles 1993, 36, 2035-2050.
-
(1993)
Heterocycles
, vol.36
, pp. 2035-2050
-
-
Ikota, N.1
-
126
-
-
0343035759
-
-
R. Csuk, M. Kühn, D. Ströhl, Tetrahedron 1997, 53, 1311-1322.
-
(1997)
Tetrahedron
, vol.53
, pp. 1311-1322
-
-
Csuk, R.1
Kühn, M.2
Ströhl, D.3
-
127
-
-
0001695526
-
-
P. Camps, J. Cardellach, J. Font, R. M. Ortuño, O. Ponsati, Tetrahedron 1982, 38, 2395-2402.
-
(1982)
Tetrahedron
, vol.38
, pp. 2395-2402
-
-
Camps, P.1
Cardellach, J.2
Font, J.3
Ortuño, R.M.4
Ponsati, O.5
-
128
-
-
0037062859
-
-
a) H. Takahashi, Y. Iwai, Y. Hitomi, S. Ikegami, Org. Lett. 2002, 4, 2401-2403;
-
(2002)
Org. Lett
, vol.4
, pp. 2401-2403
-
-
Takahashi, H.1
Iwai, Y.2
Hitomi, Y.3
Ikegami, S.4
-
129
-
-
0037424733
-
-
b) M. J. Seo, J. An, J. H. Shim, G. Kim, Tetrahedron Lett. 2003, 44, 3051-3052.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 3051-3052
-
-
Seo, M.J.1
An, J.2
Shim, J.H.3
Kim, G.4
-
131
-
-
33846498149
-
-
The assigned stereochemistries were supported by NOESY experiments. Compound 40: Spatial correlations were observed for 2-H (δH 4.10)/Meb (δH 1.46, and for 3-H (δH 4.45)/Mea (δH 1.30)/4-H (δH 4.66, Compound 41: Spatial correlations were observed for: 3-H (δH 4.36)/4a-H (δH 3.51) and 4-Ha (δH 1.40, 5-H (δH 4.24, Compound 42: Spatial correlations were observed for: CH2TMS (δH 1-21 and 0.88)/4a-H (δH 3.58, for 4a-H (δH 3.58)/Meb (δH 1.55, and for 6-H (δH 4.75)/Mea δH 1.36, δH in ppm
-
H in ppm].
-
-
-
-
132
-
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33846490978
-
-
The assigned stereochemistry for compound 43 was also supported by NOESY experiments. Spatial correlations were observed for 2-H (δH 4.43) and Meb (δH 1-45, for CHaHbCOPh (δH 3.18)/3-H (δH 4.70, for 3-H (δH 4.70)/Mea (δH 1.30)/4-H (δH 4.82, and for 4-H (δH 4.82)/CHaHbCOPh δH 3.44, δH in ppm
-
H in ppm].
-
-
-
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