-
1
-
-
0027301895
-
-
(a) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Tetrahedron 1993, 49, 8645.
-
(1993)
Tetrahedron
, vol.49
, pp. 8645
-
-
Blackman, A.J.1
Li, C.2
Hockless, D.C.R.3
Skelton, B.W.4
White, A.H.5
-
4
-
-
18744367659
-
-
in press
-
For a detailed account on efforts involving the cylindricine synthesis, see: Liu, J.; Hsung, R. P. ChemTracts 2005, 18, in press.
-
(2005)
ChemTracts
, vol.18
-
-
Liu, J.1
Hsung, R.P.2
-
5
-
-
0000932594
-
-
For the first two total syntheses of (±)-cylindricines, see: (a) Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 5630
-
-
Snider, B.B.1
Liu, T.2
-
7
-
-
0344436088
-
-
For the total synthesis of (-)-cylindricines, see: (a) Molander, G. A.; Ronn, M. J. Org. Chem. 1999, 64, 5183.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 5183
-
-
Molander, G.A.1
Ronn, M.2
-
8
-
-
4544303068
-
-
(b) Canesi, S.; Bouchu, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2004, 43, 4336.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 4336
-
-
Canesi, S.1
Bouchu, D.2
Ciufolini, M.A.3
-
9
-
-
0348041999
-
-
For recent syntheses of (+)-cylindricines, see: (a) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599.
-
(2003)
Org. Lett.
, vol.5
, pp. 4599
-
-
Trost, B.M.1
Rudd, M.T.2
-
10
-
-
3242808880
-
-
(b) Arai, T.; Abe, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2004, 45, 5921.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 5921
-
-
Arai, T.1
Abe, H.2
Aoyagi, S.3
Kibayashi, C.4
-
11
-
-
18744396201
-
-
See ref 17
-
(c) See ref 17.
-
-
-
-
12
-
-
2942574530
-
-
For reviews, see: (a) 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
-
16
-
-
0032482080
-
-
(e) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 1044
-
-
Arend, M.1
Westermann, B.2
Risch, N.3
-
18
-
-
0028280842
-
-
For isolation of lepadiformine, see: Biard, J. F.; Guyot, S.; Roussakis, C.; Verbist, J. F.; Vercauteren, J.; Weber, J. F.; Boukef, K. Tetrahedron Lett. 1994, 35, 2691.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 2691
-
-
Biard, J.F.1
Guyot, S.2
Roussakis, C.3
Verbist, J.F.4
Vercauteren, J.5
Weber, J.F.6
Boukef, K.7
-
19
-
-
0037241493
-
-
(a) For a detailed account on efforts involving the lepadiformine synthesis, see: (a) Weinreb, S. M. Acc. Chem. Res. 2003, 36, 59.
-
(2003)
Acc. Chem. Res.
, vol.36
, pp. 59
-
-
Weinreb, S.M.1
-
20
-
-
0345528025
-
-
(b) Also see: Kibayashi, C.; Aoyagi, S.; Abe, H. Bull. Chem. Soc. Jpn. 2003, 76, 2059.
-
(2003)
Bull. Chem. Soc. Jpn.
, vol.76
, pp. 2059
-
-
Kibayashi, C.1
Aoyagi, S.2
Abe, H.3
-
21
-
-
0033524881
-
-
(a) Werner, K. M.; De Los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 686.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 686
-
-
Werner, K.M.1
De Los Santos, J.M.2
Weinreb, S.M.3
Shang, M.4
-
22
-
-
0033603519
-
-
(b) Werner, K. M.; De Los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 4865.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 4865
-
-
Werner, K.M.1
De Los Santos, J.M.2
Weinreb, S.M.3
Shang, M.4
-
23
-
-
0030907069
-
-
(a) Pearson, W. H.; Barta, N. S.; Kampf, J. W. Tetrahedron Lett. 1997, 38, 3369.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 3369
-
-
Pearson, W.H.1
Barta, N.S.2
Kampf, J.W.3
-
25
-
-
0034685209
-
-
(a) Abe, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2000, 41, 1205.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 1205
-
-
Abe, H.1
Aoyagi, S.2
Kibayashi, C.3
-
26
-
-
0034679048
-
-
(b) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 4583
-
-
Abe, H.1
Aoyagi, S.2
Kibayashi, C.3
-
27
-
-
0037118888
-
-
For (-)-lepadiformine, see: (c) Abe, H.; Aoyagi, S.; Kibayashi, C. Angew. Chem., Int. Ed. 2002, 41, 3017.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 3017
-
-
Abe, H.1
Aoyagi, S.2
Kibayashi, C.3
-
28
-
-
18744377330
-
-
See ref 17
-
(d) See ref 17.
-
-
-
-
29
-
-
0037077015
-
-
For a recent total synthesis of (-)-lepadiformine, see: (a) Sun, P.; Sun, C.; Weinreb, S. M. J. Org. Chem. 2002, 67, 4337.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 4337
-
-
Sun, P.1
Sun, C.2
Weinreb, S.M.3
-
30
-
-
0035513471
-
-
(b) Sun, P.; Sun, C.; Weinreb, S. M. Org. Lett. 2001, 3, 3507.
-
(2001)
Org. Lett.
, vol.3
, pp. 3507
-
-
Sun, P.1
Sun, C.2
Weinreb, S.M.3
-
31
-
-
0035515394
-
-
For a recent total synthesis of (±)-lepadiformine, see: Greshock, T. J.; Funk, R. L. Org. Lett. 2001, 3, 3511.
-
(2001)
Org. Lett.
, vol.3
, pp. 3511
-
-
Greshock, T.J.1
Funk, R.L.2
-
33
-
-
0000564844
-
-
For some examples of natural product synthesis that employ tandem Mannich strategy, see: (a) Corey, E. J.; Balanson, R. D. J. Am. Chem Soc. 1974, 96, 6516.
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 6516
-
-
Corey, E.J.1
Balanson, R.D.2
-
35
-
-
0025265124
-
-
(c) Ihara, M.; Suzuki, M.; Fukumoto, K.; Kabuto, C. J. Am. Chem. Soc. 1990, 112, 1164.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 1164
-
-
Ihara, M.1
Suzuki, M.2
Fukumoto, K.3
Kabuto, C.4
-
36
-
-
0345938817
-
-
(d) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H. Heterocycles 1994, 37, 933.
-
(1994)
Heterocycles
, vol.37
, pp. 933
-
-
Takahashi, I.1
Tsuzuki, M.2
Yokota, H.3
Kitajima, H.4
-
37
-
-
18744362835
-
-
(e) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Morita, T.; Kitajima, H. Heterocycles 1988, 43, 71.
-
(1988)
Heterocycles
, vol.43
, pp. 71
-
-
Takahashi, I.1
Tsuzuki, M.2
Yokota, H.3
Morita, T.4
Kitajima, H.5
-
38
-
-
0000877160
-
-
(f) Scott, R. W.; Epperson, J.; Heathcock, C. H. J. Org. Chem. 1998, 63, 5001.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 5001
-
-
Scott, R.W.1
Epperson, J.2
Heathcock, C.H.3
-
39
-
-
8744262719
-
-
Liu, J.; Hsung, R. P.; Peters, S. D. Org. Lett. 2004, 6, 3989.
-
(2004)
Org. Lett.
, vol.6
, pp. 3989
-
-
Liu, J.1
Hsung, R.P.2
Peters, S.D.3
-
40
-
-
13444249603
-
-
For a recent account employing a similar concept of achieving total syntheses of both (-)-lepadiformine and (+)-cylindricines C-E via a aza-spirocyclic common intermediate, see: Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2005, 127, 1473.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 1473
-
-
Abe, H.1
Aoyagi, S.2
Kibayashi, C.3
-
42
-
-
77957077000
-
-
Brossi, A., Ed.; Academic Press: San Diego, CA
-
(a) For a related review, see: (a) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Brossi, A., Ed.; Academic Press: San Diego, CA, 1988; Vol. 2, pp 271-339.
-
(1988)
Comprehensive Organic Synthesis
, vol.2
, pp. 271-339
-
-
Hiemstra, H.1
Speckamp, W.N.2
-
43
-
-
0141631601
-
-
For some examples, see: (b) Chao, W.; Waldman, J. H.; Weinreb, S. M. Org. Lett. 2003, 5, 2915.
-
(2003)
Org. Lett.
, vol.5
, pp. 2915
-
-
Chao, W.1
Waldman, J.H.2
Weinreb, S.M.3
-
44
-
-
0141765923
-
-
(c) Dobbs, A.; Guesné, S. J. J.; Martinovic, S.; Coles, S. J.; Hursthouse, M. B. J. Org. Chem. 2003, 68, 7880.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 7880
-
-
Dobbs, A.1
Guesné, S.J.J.2
Martinovic, S.3
Coles, S.J.4
Hursthouse, M.B.5
-
47
-
-
0000248631
-
-
For examples of alkynes in aza-Prins-type cyclizations, see: (a) Schoemaker, H. E.; Boer-Terpstra, Tj.; Dijkink, J.; Speckamp, W. N. Tetrahedron 1980, 36, 143.
-
(1980)
Tetrahedron
, vol.36
, pp. 143
-
-
Schoemaker, H.E.1
Boer-Terpstra, Tj.2
Dijkink, J.3
Speckamp, W.N.4
-
51
-
-
0000034033
-
-
(e) Wijnberg, B. P.; Speckamp, W. N.; Oostveen, A. R. C. Tetrahedron 1882, 38, 209.
-
(1882)
Tetrahedron
, vol.38
, pp. 209
-
-
Wijnberg, B.P.1
Speckamp, W.N.2
Oostveen, A.R.C.3
-
52
-
-
0342623561
-
-
(f) Hamersma, J. A. M.; Nossin, P. M. M.; Speckamp, W. N. Tetrahedron 1885, 41, 1999.
-
(1885)
Tetrahedron
, vol.41
, pp. 1999
-
-
Hamersma, J.A.M.1
Nossin, P.M.M.2
Speckamp, W.N.3
-
53
-
-
18744404635
-
-
note
-
The use of alkenes for the aza-Prins-type N-acyliminium addition in this case also failed. Please refer to ref 6c for numerous examples of addition of alkenes to N-acyliminium (diagram presented)
-
-
-
-
54
-
-
18744409200
-
-
note
-
Kibayashi also reported similar difficulties with alkenes and unsubstituted dienes: see ref 17.
-
-
-
-
55
-
-
18744412762
-
-
note
-
2O quenching instead of the desired the γ-proton.
-
-
-
-
57
-
-
33947483025
-
-
(b) Wharton, P. S.; Dunny, S.; Krebs, L. S. J. Org. Chem. 1964, 29, 958.
-
(1964)
J. Org. Chem.
, vol.29
, pp. 958
-
-
Wharton, P.S.1
Dunny, S.2
Krebs, L.S.3
-
59
-
-
84985185605
-
-
(b) Schult-Elte, K. H.; Rautenstrauch, V.; Ohloff, G. Helv. Chim Acta 1971, 54, 1805.
-
(1971)
Helv. Chim. Acta
, vol.54
, pp. 1805
-
-
Schult-Elte, K.H.1
Rautenstrauch, V.2
Ohloff, G.3
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