-
1
-
-
29944444144
-
-
Cordell, G. A., Ed.; Academic Press: San Diego, CA
-
Saxton, J. E. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1998; Vol. 51, pp 1-197.
-
(1998)
The Alkaloids: Chemistry and Biology
, vol.51
, pp. 1-197
-
-
Saxton, J.E.1
-
3
-
-
33746884988
-
-
Saxton, J. E., Ed.; Wiley: Chichester; Chapter 1
-
(b) Herbert, R. B. In The Monoterpenoid Indole Alkaloids; Supplement to Vol. 25, part 4 of The Chemistry of Heterocyclic Compounds; Saxton, J. E., Ed.; Wiley: Chichester, 1994; Chapter 1.
-
(1994)
The Monoterpenoid Indole Alkaloids; Supplement to Vol. 25, Part 4 of The Chemistry of Heterocyclic Compounds
, vol.25
-
-
Herbert, R.B.1
-
5
-
-
0001004640
-
-
For the first synthesis of aspidospermine and vindoline, see: (a) Stork, G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872.
-
(1963)
J. Am. Chem. Soc.
, vol.85
, pp. 2872
-
-
Stork, G.1
Dolfini, J.E.2
-
6
-
-
33847801572
-
-
(b) Ando, M.; Buchi, G.; Ohnuma, T. J. Am. Chem. Soc. 1975, 97, 6880.
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 6880
-
-
Ando, M.1
Buchi, G.2
Ohnuma, T.3
-
7
-
-
0002457796
-
-
For some select methods to synthesize the pentacyclic framework of aspidospermidine (1), see: (a) Camerman, A.; Camerman, N.; Kutney, J. P.; Piers, E.; Trotter, J. Tetrahedron Lett. 1965, 637.
-
(1965)
Tetrahedron Lett.
, pp. 637
-
-
Camerman, A.1
Camerman, N.2
Kutney, J.P.3
Piers, E.4
Trotter, J.5
-
9
-
-
0015952048
-
-
(c) Laronze, J.-Y.; Laronze-Fontaine, J.; Lévy, J.; Le Men, J. Tetrahedron Lett. 1974, 491.
-
(1974)
Tetrahedron Lett.
, pp. 491
-
-
Laronze, J.-Y.1
Laronze-Fontaine, J.2
Lévy, J.3
Le Men, J.4
-
10
-
-
0019775986
-
-
(d) Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T. J. Am. Chem. Soc. 1981, 103, 6990.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 6990
-
-
Ban, Y.1
Yoshida, K.2
Goto, J.3
Oishi, T.4
-
11
-
-
33845553662
-
-
(e) Gallagher, T.; Magnus, P.; Huffman, J. J. Am. Chem. Soc. 1982, 104, 1140.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 1140
-
-
Gallagher, T.1
Magnus, P.2
Huffman, J.3
-
13
-
-
0000583739
-
-
(g) Mandal, S. B.; Giri, V. S.; Sabeena, M. S.; Pakrashi, S. C. J. Org. Chem. 1988, 53, 4236.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 4236
-
-
Mandal, S.B.1
Giri, V.S.2
Sabeena, M.S.3
Pakrashi, S.C.4
-
15
-
-
0025021186
-
-
(i) Node, M.; Nagasawa, H.; Fugi, K. J. Org. Chem. 1990, 55, 517.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 517
-
-
Node, M.1
Nagasawa, H.2
Fugi, K.3
-
16
-
-
32444434281
-
-
(j) Le Menez, P.; Kunesch, N.; Lui, S.; Wenkert, E. J. Org. Chem. 1991, 56, 2915.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2915
-
-
Le Menez, P.1
Kunesch, N.2
Lui, S.3
Wenkert, E.4
-
19
-
-
0029801252
-
-
(m) Forns, P.; Diez, A.; Rubiralta, M. J. Org. Chem. 1996, 61, 7882.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 7882
-
-
Forns, P.1
Diez, A.2
Rubiralta, M.3
-
21
-
-
0001149012
-
-
(o) Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. J. Chem. Soc., Perkin Trans. 1 1999, 995.
-
(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 995
-
-
Callaghan, O.1
Lampard, C.2
Kennedy, A.R.3
Murphy, J.A.4
-
22
-
-
0034199893
-
-
(p) Iyengar, R.; Schildknegt, K.; Aubé, J. Org. Lett. 2000, 2, 1625.
-
(2000)
Org. Lett.
, vol.2
, pp. 1625
-
-
Iyengar, R.1
Schildknegt, K.2
Aubé, J.3
-
25
-
-
0036570864
-
-
(s) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 4628
-
-
Kozmin, S.A.1
Iwama, T.2
Huang, Y.3
Rawal, V.H.4
-
27
-
-
0037073156
-
-
(u) Marino, J. P.; Rubio, M. B.; Cao, G.; de Dios, A. J. Am. Chem. Soc. 2002, 124, 13398.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13398
-
-
Marino, J.P.1
Rubio, M.B.2
Cao, G.3
De Dios, A.4
-
28
-
-
3242686921
-
-
(v) Gnecco, D.; Vázquez, E.; Galindo, A.; Terán, J. L.; Bernès, S.; Enríquez, R. G. Arkivoc 2003, 11, 185.
-
(2003)
Arkivoc
, vol.11
, pp. 185
-
-
Gnecco, D.1
Vázquez, E.2
Galindo, A.3
Terán, J.L.4
Bernès, S.5
Enríquez, R.G.6
-
29
-
-
1642365909
-
-
(w) Tanino, H.; Fukuishi, T.; Ushiyama, M.; Okada, K. Tetrahedron 2004, 60, 3273.
-
(2004)
Tetrahedron
, vol.60
, pp. 3273
-
-
Tanino, H.1
Fukuishi, T.2
Ushiyama, M.3
Okada, K.4
-
31
-
-
0039805660
-
-
Yates, P.; MacLachlan, F. N.; Rae, I. D.; Rosenberger, M.; Szabo, A. G.; Willis, C. R.; Cava, M. P.; Behforouz, M.; Lakshmikantham, M. V.; Ziegler, W. J. Am. Chem. Soc. 1973, 95, 7842.
-
(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 7842
-
-
Yates, P.1
MacLachlan, F.N.2
Rae, I.D.3
Rosenberger, M.4
Szabo, A.G.5
Willis, C.R.6
Cava, M.P.7
Behforouz, M.8
Lakshmikantham, M.V.9
Ziegler, W.10
-
33
-
-
0017252944
-
-
(b) Cheng, P.-T.; Nyburg, S. C.; MacLachlan, F. N.; Yates, P. Can. J. Chem. 1976, 54, 726.
-
(1976)
Can. J. Chem.
, vol.54
, pp. 726
-
-
Cheng, P.-T.1
Nyburg, S.C.2
MacLachlan, F.N.3
Yates, P.4
-
34
-
-
0141785817
-
-
(a) Cava, M. P.; Talapatra, S. K.; Nomura, K.; Weisbach, J. A.; Douglas, B.; Shoop, E. C. Chem. Ind. (London) 1963, 1242.
-
(1963)
Chem. Ind. (London)
, pp. 1242
-
-
Cava, M.P.1
Talapatra, S.K.2
Nomura, K.3
Weisbach, J.A.4
Douglas, B.5
Shoop, E.C.6
-
35
-
-
0141562482
-
-
(b) Cava, M. P.; Talapatra, S. K.; Yates, P.; Rosenberger, M.; Szabo, A. G.; Douglas, B.; Raffuaf, R. F.; Shoop, E. C.; Weisbach, J. A. Chem. Ind. (London) 1963, 1875.
-
(1963)
Chem. Ind. (London)
, pp. 1875
-
-
Cava, M.P.1
Talapatra, S.K.2
Yates, P.3
Rosenberger, M.4
Szabo, A.G.5
Douglas, B.6
Raffuaf, R.F.7
Shoop, E.C.8
Weisbach, J.A.9
-
36
-
-
0141785816
-
-
(c) Rae, I. D.; Rosenberger, M.; Szabo, A. G.; Willis, C. R.; Yates, P.; Zacharias, D. E.; Jeffrey, G. A.; Douglas, B.; Kirkpatrick, J.-L.; Weisbach, J. A. J. Am. Chem. Soc. 1967, 89, 3061.
-
(1967)
J. Am. Chem. Soc.
, vol.89
, pp. 3061
-
-
Rae, I.D.1
Rosenberger, M.2
Szabo, A.G.3
Willis, C.R.4
Yates, P.5
Zacharias, D.E.6
Jeffrey, G.A.7
Douglas, B.8
Kirkpatrick, J.-L.9
Weisbach, J.A.10
-
37
-
-
0033591940
-
-
He, F.; Bo, Y.; Altom, J. D.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 6771.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 6771
-
-
He, F.1
Bo, Y.2
Altom, J.D.3
Corey, E.J.4
-
38
-
-
0041350409
-
-
(a) Sumi, S.; Matsumoto, S.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 1891.
-
(2003)
Org. Lett.
, vol.5
, pp. 1891
-
-
Sumi, S.1
Matsumoto, S.2
Tokuyama, H.3
Fukuyama, T.4
-
39
-
-
0141594838
-
-
(b) Sumi, S.; Matsumoto, K.; Tokuyama, H.; Fukuyama, T. Tetrahedron 2003, 59, 8571.
-
(2003)
Tetrahedron
, vol.59
, pp. 8571
-
-
Sumi, S.1
Matsumoto, K.2
Tokuyama, H.3
Fukuyama, T.4
-
40
-
-
0000352286
-
-
(a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 3127
-
-
Fukuyama, T.1
Chen, X.2
Peng, G.3
-
41
-
-
0034050746
-
-
(b) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429.
-
(2000)
Synthesis
, pp. 429
-
-
Tokuyama, H.1
Kaburagi, Y.2
Chen, X.3
Fukuyama, T.4
-
42
-
-
0034847193
-
-
(c) Tokuyama, H.; Watanabe, M.; Hayashi, Y.; Kurokawa, T.; Peng, G.; Fukuyama, T. Synlett 2001, 1403.
-
(2001)
Synlett
, pp. 1403
-
-
Tokuyama, H.1
Watanabe, M.2
Hayashi, Y.3
Kurokawa, T.4
Peng, G.5
Fukuyama, T.6
-
43
-
-
0033582790
-
-
(d) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 1519
-
-
Kobayashi, S.1
Peng, G.2
Fukuyama, T.3
-
45
-
-
9644285669
-
-
Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
-
(1975)
Tetrahedron Lett.
, vol.16
, pp. 4467
-
-
Sonogashira, K.1
Tohda, Y.2
Hagihara, N.3
-
50
-
-
2442647730
-
-
(e) Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 3735
-
-
Padwa, A.1
Brodney, M.A.2
Lynch, S.M.3
Rashatasakhon, P.4
Wang, Q.5
Zhang, H.6
-
52
-
-
26444541805
-
-
and references therein
-
Boger and co-workers have recently described an alternate approach to onium ylides based on a [4+2]-cycloaddition of 1,3,4-oxadiazoles followed by a thermal extrusion of nitrogen and have elegantly exploited this chemistry for the construction of a variety of aspidosperma alkaloid targets. See: Choi, Y.; Ishikawa, H.; Velcicky, J.; Elliott, G. I.; Miller, M. M.; Boger, D. L. Org. Lett. 2005, 7, 4539 and references therein.
-
(2005)
Org. Lett.
, vol.7
, pp. 4539
-
-
Choi, Y.1
Ishikawa, H.2
Velcicky, J.3
Elliott, G.I.4
Miller, M.M.5
Boger, D.L.6
-
56
-
-
15444366308
-
-
(d) Padwa, A.; Lynch, S. M.; Mejía-Oneto, J. M.; Zhang, H. J. Org. Chem. 2005, 70, 2206.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 2206
-
-
Padwa, A.1
Lynch, S.M.2
Mejía-Oneto, J.M.3
Zhang, H.4
-
58
-
-
0001379168
-
-
(b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709.
-
(1980)
J. Org. Chem.
, vol.45
, pp. 2709
-
-
Odle, R.1
Blevins, B.2
Ratcliff, M.3
Hegedus, L.S.4
-
60
-
-
84969808662
-
-
Brooks, D. W.; Lu, D. L.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1979, 18, 72.
-
(1979)
Angew. Chem., Int. Ed. Engl.
, vol.18
, pp. 72
-
-
Brooks, D.W.1
Lu, D.L.2
Masamune, S.3
-
62
-
-
0001241137
-
-
(b) Regitz, M.; Hocker, J.; Liedhegener, A. Org. Synth. 1973, 5, 179.
-
(1973)
Org. Synth.
, vol.5
, pp. 179
-
-
Regitz, M.1
Hocker, J.2
Liedhegener, A.3
-
63
-
-
33746917012
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note
-
15 the exo cycloadducts 11 and 22 were the exclusive products isolated from the Rh(II)-catalyzed reaction. We assume that the bulky tert-butyl ester functionality blocks the endo approach thereby resulting in cycloaddition taking place from the less-congested exo face.
-
-
-
-
64
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33746885345
-
-
note
-
The authors have deposited coordinates for structure 24 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, B2 1EZ, U.K.
-
-
-
-
65
-
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85077854948
-
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For a review of dealkoxycarbonylations, see: Krapcho, A. P. Synthesis 1982, 805 and 893.
-
(1982)
Synthesis
, pp. 805
-
-
Krapcho, A.P.1
-
67
-
-
0028326930
-
-
(b) Davis, F. A.; Clark, C.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1994, 59, 1184.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 1184
-
-
Davis, F.A.1
Clark, C.2
Kumar, A.3
Chen, B.-C.4
-
68
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33746880898
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note
-
Structure 25 was established on the basis of an X-ray crystal structure analysis. A more detailed study of this unusual rearrangement is currently underway in our laboratory.
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