-
1
-
-
77956830705
-
-
Cordell, G. A, Ed, Academic Press: San Diego, Chap. 4, p
-
Tsuda, Y.; Sano, T. In The Alkaloids: Chemistry and Pharmacology, Vol. 48; Cordell, G. A., Ed.; Academic Press: San Diego, 1996; Chap. 4, p 249.
-
(1996)
The Alkaloids: Chemistry and Pharmacology
, vol.48
, pp. 249
-
-
Tsuda, Y.1
Sano, T.2
-
2
-
-
33744954743
-
-
and references cited therein
-
(b) Bentley, K. W. Nat. Prod. Rep. 2006, 23, 444, and references cited therein.
-
(2006)
Nat. Prod. Rep
, vol.23
, pp. 444
-
-
Bentley, K.W.1
-
3
-
-
0033978692
-
-
For a review, see reference 1a. For some recent examples, see: (a) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235.
-
For a review, see reference 1a. For some recent examples, see: (a) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235.
-
-
-
-
5
-
-
0034697415
-
-
(c) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc. Perkin 1 2000, 1505.
-
(2000)
J. Chem. Soc. Perkin 1
, pp. 1505
-
-
Hosoi, S.1
Nagao, M.2
Tsuda, Y.3
Isobe, K.4
Sano, T.5
Ohta, T.6
-
6
-
-
0034800212
-
-
(d) Jousse-Karinthi, C.; Riche, C.; Chiaroni, A.; Desmaele, D. Eur. J. Org. Chem. 2001, 3631.
-
(2001)
Eur. J. Org. Chem
, pp. 3631
-
-
Jousse-Karinthi, C.1
Riche, C.2
Chiaroni, A.3
Desmaele, D.4
-
7
-
-
0037184882
-
-
(e) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464.
-
(2002)
J. Org. Chem
, vol.67
, pp. 9464
-
-
Allin, S.M.1
James, S.L.2
Elsegood, M.R.J.3
Martin, W.P.4
-
9
-
-
0037462393
-
-
(g) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312.
-
(2003)
J. Org. Chem
, vol.68
, pp. 312
-
-
Chikaoka, S.1
Toyao, A.2
Ogasawara, M.3
Tamura, O.4
Ishibashi, H.5
-
10
-
-
0141794013
-
-
(h) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 7803
-
-
Gill, C.1
Greenhalgh, D.A.2
Simpkins, N.S.3
-
13
-
-
29044435289
-
-
(j) Blake, A. J.; Gill, C.; Greenhalgh, D. A.; Simpkins, S.; Zhang, F. Synthesis 2005, 3287.
-
(2005)
Synthesis
, pp. 3287
-
-
Blake, A.J.1
Gill, C.2
Greenhalgh, D.A.3
Simpkins, S.4
Zhang, F.5
-
14
-
-
33745725808
-
-
(k) Gao, S.; Tu, Y. Q.; Hu, X.; Wang, S.; Hua, R.; JIang, Y.; Zhao, Y.; Fan, X.; Zhang, S. Org. Lett. 2006, 8, 2373.
-
(2006)
Org. Lett
, vol.8
, pp. 2373
-
-
Gao, S.1
Tu, Y.Q.2
Hu, X.3
Wang, S.4
Hua, R.5
JIang, Y.6
Zhao, Y.7
Fan, X.8
Zhang, S.9
-
15
-
-
0030597180
-
-
Manteca, I.; Sotomayor, N.; Lete, E. Tetrahedron Lett. 1996, 33, 7841.
-
(1996)
Tetrahedron Lett
, vol.33
, pp. 7841
-
-
Manteca, I.1
Sotomayor, N.2
Lete, E.3
-
16
-
-
0030593585
-
-
(b) Collado, M. I.; Sotomayor, N.; Villa, M.-J.; Lete, E. Tetrahedron Lett. 1996, 37, 6193.
-
(1996)
Tetrahedron Lett
, vol.37
, pp. 6193
-
-
Collado, M.I.1
Sotomayor, N.2
Villa, M.-J.3
Lete, E.4
-
17
-
-
0001157440
-
-
(c) Collado, M. I.; Manteca, I.; Sotomayor, N.; Villa, M. J.; Lete, E. J. Org. Chem. 1997, 62, 2080.
-
(1997)
J. Org. Chem
, vol.62
, pp. 2080
-
-
Collado, M.I.1
Manteca, I.2
Sotomayor, N.3
Villa, M.J.4
Lete, E.5
-
18
-
-
0032191024
-
-
(d) Manteca, I.; Etxarri, B.; Ardeo, A.; Arrasate, S.; Osante, I.; Sotomayor, N.; Lete, E. Tetrahedron 1998, 54, 12361.
-
(1998)
Tetrahedron
, vol.54
, pp. 12361
-
-
Manteca, I.1
Etxarri, B.2
Ardeo, A.3
Arrasate, S.4
Osante, I.5
Sotomayor, N.6
Lete, E.7
-
21
-
-
0142174551
-
-
Hodgson, D. M, Ed, Springer: Berlin
-
(c) Hodgson, D. M., Ed., Organolithiums in Enantioselective Synthesis, Topics in Organometallic Chemistry; Springer: Berlin, 2003; Vol. 5.
-
(2003)
Organolithiums in Enantioselective Synthesis, Topics in Organometallic Chemistry
, vol.5
-
-
-
22
-
-
85069242295
-
-
Rappoport, Z.; Marek, I., Eds. The Chemistry of Organolithium Compounds; Patai Series: The Chemistry of Functional Groups, Rappoport, Z.; Ed., Wiley: Chichester, 2004.
-
(e) Rappoport, Z.; Marek, I., Eds. The Chemistry of Organolithium Compounds; Patai Series: The Chemistry of Functional Groups, Rappoport, Z.; Ed., Wiley: Chichester, 2004.
-
-
-
-
23
-
-
46549103031
-
-
For reviews on N-acyliminium ion cyclizations, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
-
For reviews on N-acyliminium ion cyclizations, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
-
-
-
-
24
-
-
77957077000
-
-
Academic Press, New York
-
(b) Hiemstra, H.; Speckamp, W. N. in The Alkaloids; Academic Press, New York, 1988; Vol. 32, p 271.
-
(1988)
The Alkaloids
, vol.32
, pp. 271
-
-
Hiemstra, H.1
Speckamp, W.N.2
-
25
-
-
0001673091
-
-
Trost, B. M, Fleming, I. Eds, Pergamon: Oxford
-
(c) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds., Pergamon: Oxford, 1991; Vol. 2, p 1047.
-
(1991)
Comprehensive Organic Synthesis
, vol.2
, pp. 1047
-
-
Hiemstra, H.1
Speckamp, W.N.2
-
26
-
-
85069249497
-
-
de Koning, H.; Speckamp, W. N. In Stereoselective Synthesis [Houben-Weyl], Helmchen, G.; Hoffmann, R. W.; Muzler, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996, Workbench Ed. E21, 3, p 1952.
-
(d) de Koning, H.; Speckamp, W. N. In Stereoselective Synthesis [Houben-Weyl], Helmchen, G.; Hoffmann, R. W.; Muzler, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996, Workbench Ed. E21, Vol. 3, p 1952.
-
-
-
-
29
-
-
1842430777
-
-
(g) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431.
-
(2004)
Chem. Rev
, vol.104
, pp. 1431
-
-
Maryanoff, B.E.1
Zhang, H.-C.2
Cohen, J.H.3
Turchi, I.J.4
Maryanoff, C.A.5
-
30
-
-
2942574530
-
-
(h) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
-
(2004)
Chem. Rev
, vol.104
, pp. 2311
-
-
Royer, J.1
Bonin, M.2
Micouin, L.3
-
31
-
-
84906288269
-
-
Katritzky, A. R, Taylor, R. J. K, Eds, Elsevier: Oxford
-
(i) Dobbs, A. P.; Rossiter, S. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2005; Vol. 3, p 419.
-
(2005)
Comprehensive Organic Functional Group Transformations II
, vol.3
, pp. 419
-
-
Dobbs, A.P.1
Rossiter, S.2
-
32
-
-
0035911014
-
-
García, E.; Arrasate, S.; Ardeo, A.; Lete, E.; Sotomayor, N. Tetrahedron Lett. 2001, 42, 1511.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 1511
-
-
García, E.1
Arrasate, S.2
Ardeo, A.3
Lete, E.4
Sotomayor, N.5
-
34
-
-
2442705392
-
-
(c) González, I; Osante, I.; Sotomayor, N.; Lete, E J. Org. Chem. 2004, 69, 3875.
-
(2004)
J. Org. Chem
, vol.69
, pp. 3875
-
-
González, I.1
Osante, I.2
Sotomayor, N.3
Lete, E.4
-
35
-
-
28744436180
-
-
(d) García, E.; Arrasate, S.; Lete, E.; Sotomayor, N. J. Org. Chem. 2005, 70, 10368.
-
(2005)
J. Org. Chem
, vol.70
, pp. 10368
-
-
García, E.1
Arrasate, S.2
Lete, E.3
Sotomayor, N.4
-
36
-
-
14844327825
-
-
For a preliminary communication, see
-
For a preliminary communication, see: Osante, I.; Sotomayor, N.; Lete, E Lett. Org. Chem. 2004, 1, 148.
-
(2004)
Lett. Org. Chem
, vol.1
, pp. 148
-
-
Osante, I.1
Sotomayor, N.2
Lete, E.3
-
40
-
-
0000957502
-
-
Jacobsen, E. N, Pfaltz, A, Yamamoto, H. Eds, Springer: Berlin
-
(d) Yamamguchi, M. In Comprehensive Asymmetric Catalysis I-III, Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Eds.; Springer: Berlin, 1999; Vol. 3, p 1121.
-
(1999)
Comprehensive Asymmetric Catalysis I-III
, vol.3
, pp. 1121
-
-
Yamamguchi, M.1
-
42
-
-
3943106957
-
In Organolithiums in Enantioselective Synthesis
-
Hodgson, D. M, Ed, Springer: Berlin
-
(f) Iguchi, M.; Yamada, K.; Tomioka, K. In Organolithiums in Enantioselective Synthesis, Hodgson, D. M., Ed.; Topics in Organometallic Chemistry, Springer: Berlin, 2003; Vol. 5, p 21.
-
(2003)
Topics in Organometallic Chemistry
, vol.5
, pp. 21
-
-
Iguchi, M.1
Yamada, K.2
Tomioka, K.3
-
43
-
-
85069257134
-
-
Only small ammounts of the desired erythrinane (<4%) were obtained. Manteca, I. Ph. D. Dissertation, Universidad del País Vasco, Bilbao (Spain), 1997.
-
Only small ammounts of the desired erythrinane (<4%) were obtained. Manteca, I. Ph. D. Dissertation, Universidad del País Vasco, Bilbao (Spain), 1997.
-
-
-
-
44
-
-
0034904455
-
-
Recent reviews: a
-
Recent reviews: (a) Yus, M. Synlett 2001, 1197.
-
(2001)
Synlett
, pp. 1197
-
-
Yus, M.1
-
46
-
-
2942530950
-
-
(c) Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
-
(2004)
Chem. Rev
, vol.104
, pp. 2667
-
-
Chinchilla, R.1
Nájera, C.2
Yus, M.3
-
47
-
-
14844291428
-
-
(d) Chinchilla, R.; Nájera, C.; Yus, M. Tetrahedron 2005, 56, 3139.
-
(2005)
Tetrahedron
, vol.56
, pp. 3139
-
-
Chinchilla, R.1
Nájera, C.2
Yus, M.3
-
48
-
-
0034685859
-
-
See, for instance
-
See, for instance: Amat, M.; Bosch, J.; Hidalgo, J.; Cantó, M.; Pérez, M.; Llor, N.; Molins, E.; Miratvilles, C.; Orozco, M.; Luque, J. J. Org. Chem. 2000, 65, 3074.
-
(2000)
J. Org. Chem
, vol.65
, pp. 3074
-
-
Amat, M.1
Bosch, J.2
Hidalgo, J.3
Cantó, M.4
Pérez, M.5
Llor, N.6
Molins, E.7
Miratvilles, C.8
Orozco, M.9
Luque, J.10
-
49
-
-
0035929396
-
-
Fleming, F. F.; Funk, L.; Altundas, R.; Tu, Y. J. Org. Chem. 2001, 66, 6502.
-
(2001)
J. Org. Chem
, vol.66
, pp. 6502
-
-
Fleming, F.F.1
Funk, L.2
Altundas, R.3
Tu, Y.4
-
50
-
-
33845552740
-
-
For reviews on Parham cyclization, see: a
-
For reviews on Parham cyclization, see: (a) Parham, W. E.; Bradsher, C. K. Acc. Chem. Res. 1982, 15, 300.
-
(1982)
Acc. Chem. Res
, vol.15
, pp. 300
-
-
Parham, W.E.1
Bradsher, C.K.2
-
51
-
-
0002148313
-
-
Abel, E. W, Stone, F. G. A, Wilkinson, G, Eds, Pergamon: Oxford
-
(b) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 11; p 66.
-
(1995)
Comprehensive Organometallic Chemistry II
, vol.11
, pp. 66
-
-
Gray, M.1
Tinkl, M.2
Snieckus, V.3
-
52
-
-
0141775489
-
-
Atanassi, O, Spinelli, D. Eds, Italian Society of Chemistry: Roma
-
(c) Ardeo, A.; Collado, M. I.; Osante, I.; Ruiz, J.; Sotomayor, N.; Lete, E. In Targets in Heterocyclic Systems, Atanassi, O.; Spinelli, D. Eds.; Italian Society of Chemistry: Roma, 2001, Vol. 5, p 393.
-
(2001)
Targets in Heterocyclic Systems
, vol.5
, pp. 393
-
-
Ardeo, A.1
Collado, M.I.2
Osante, I.3
Ruiz, J.4
Sotomayor, N.5
Lete, E.6
-
55
-
-
33646792011
-
-
Vicario, J. L, Badía, D, Carrillo, L, Eds, Research Signpost: India
-
(f) Arrasate, S.; Sotomayor , N.; Lete, E. In New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles , Vicario, J. L.; Badía, D.; Carrillo, L.; Eds., Research Signpost: India, 2005, p 223.
-
(2005)
New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles
, pp. 223
-
-
Arrasate, S.1
Sotomayor, N.2
Lete, E.3
-
56
-
-
0000174207
-
-
Hosomi, A.; Shirahata, A.; Sakurai, H. Tetrahedron Lett. 1978, 33, 3043.
-
(1978)
Tetrahedron Lett
, vol.33
, pp. 3043
-
-
Hosomi, A.1
Shirahata, A.2
Sakurai, H.3
-
57
-
-
0000300250
-
-
(b) Majetich, G.; Casares,. A. M.; Chapman, D.; Behnke, M.J. Org. Chem. 1986, 51, 1745.
-
(1986)
J. Org. Chem
, vol.51
, pp. 1745
-
-
Majetich, G.1
Casares, A.M.2
Chapman, D.3
Behnke, M.4
-
58
-
-
0000807502
-
-
(c) Groaning, M. D.; Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1998, 63, 5517.
-
(1998)
J. Org. Chem
, vol.63
, pp. 5517
-
-
Groaning, M.D.1
Brengel, G.P.2
Meyers, A.I.3
-
60
-
-
85069250111
-
-
Pyrroloisoquinoline 11 has been previously prepared by allyl-lithium addition followed by N-acyliminium cylization with TFA see ref 3c, However, as stated there, by this route it is difficult to obtain the product in pure form due to contamination with the stannane residue of the precursor of the allyllithium. Besides, allylmagnesium chloride addition followed by α-amidoalkylation with TFA, BF3.OEt2 or TiCl4 did not give 11. In this case, allyl group is not stable under these conditions, and isomerization of the double bond occurs
-
4 did not give 11. In this case, allyl group is not stable under these conditions, and isomerization of the double bond occurs.
-
-
-
-
61
-
-
85069244547
-
-
1H decoupling experiments confirmed the stereochemistry of 12. For instance, an enhancement of the H-2 signals was observed upon irradiation on one of the methylene hydrogens of the allyl group in C-1 and vice versa. This fact, together with the absence of NOE between both allyl groups confirms they are in a trans disposition. The rest of the NOE experiments carried out were fully consistent with the proposed stereochemistry.
-
1H decoupling experiments confirmed the stereochemistry of 12. For instance, an enhancement of the H-2 signals was observed upon irradiation on one of the methylene hydrogens of the allyl group in C-1 and vice versa. This fact, together with the absence of NOE between both allyl groups confirms they are in a trans disposition. The rest of the NOE experiments carried out were fully consistent with the proposed stereochemistry.
-
-
-
-
62
-
-
0032580376
-
-
For selected reviews, see: a
-
For selected reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
-
(1998)
Tetrahedron
, vol.54
, pp. 4413
-
-
Grubbs, R.H.1
Chang, S.2
|