-
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
-
-
0028280842
-
-
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
-
5
-
-
0031012361
-
-
Patil, A. D.; Freyer, A. J.; Reichwein, R.; Carte, B.; Killmer, L. B.; Faucette, L.; Johnson, R. K.; Faulkner, D. J. Tetrahedron Lett. 1997, 38, 363.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 363
-
-
Patil, A.D.1
Freyer, A.J.2
Reichwein, R.3
Carte, B.4
Killmer, L.B.5
Faucette, L.6
Johnson, R.K.7
Faulkner, D.J.8
-
6
-
-
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
-
7
-
-
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
-
8
-
-
0035513471
-
-
(c) 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
-
9
-
-
0037077015
-
-
For their recent total syntheses of (-)-lepadiformine, see: (d) 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
-
10
-
-
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
-
12
-
-
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
-
13
-
-
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
-
14
-
-
0037118888
-
-
(c) For a synthesis of (-)-lepadiformine, see: 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
-
15
-
-
13444249603
-
-
(d) For a recent account on total syntheses of both (-)-lepadiformine and (+)-cylindricines C-E via an 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
-
16
-
-
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
-
17
-
-
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
-
19
-
-
0037034347
-
-
For total syntheses of fasicularin, see: (a) Maeng, J.-H, Funk, R. L. Org. Lett. 2002, 4, 331.
-
(2002)
Org. Lett.
, vol.4
, pp. 331
-
-
Maeng, J.-H.1
Funk, R.L.2
-
22
-
-
0000932594
-
-
For 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
-
25
-
-
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
-
26
-
-
0348041999
-
-
For a recent synthesis of (+)-cylindricines, see: (c) 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
-
27
-
-
3242808880
-
-
(d) 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
-
28
-
-
33644771766
-
-
Also see 6d.
-
(e) Also see 6d.
-
-
-
-
29
-
-
18744402534
-
-
(f) Taniguchi, T.; Tamura, O.; Uchiyama, M.; Muraoka, O.; Tanabe, G.; Ishibashi, H. Synlett 2005, 1179.
-
(2005)
Synlett
, pp. 1179
-
-
Taniguchi, T.1
Tamura, O.2
Uchiyama, M.3
Muraoka, O.4
Tanabe, G.5
Ishibashi, H.6
-
30
-
-
8744262719
-
-
For total syntheses of both (+)-cylindricines and (-)-lepadiformine via a common aza-tricyclic intermediate, see: (a) 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
-
31
-
-
18744409514
-
-
(b) Liu, J.; Swidorski, J. J.; Peter, S. D.; Hsung, R. P. J. Org. Chem. 2005, 70, 3898.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 3898
-
-
Liu, J.1
Swidorski, J.J.2
Peter, S.D.3
Hsung, R.P.4
-
34
-
-
0000279802
-
Enaminones as synthons
-
Rappoport, Z., Ed.; John Wiley & Sons: New York
-
For a review on vinylogous amide chemistry, see: Kucklander, U. Enaminones as Synthons. In The Chemistry of Functional Groups: The Chemistry of Enamines; Rappoport, Z., Ed.; John Wiley & Sons: New York, 1994; Part I, p 523.
-
(1994)
The Chemistry of Functional Groups: The Chemistry of Enamines
, Issue.PART I
, pp. 523
-
-
Kucklander, U.1
-
35
-
-
11844292757
-
-
For recent studies in this area, see: (a) Goodenough, K. M.; Moran, W. J.; Raubo, P.; Harrity, J. P. A. J. Org. Chem. 2005, 70, 207.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 207
-
-
Goodenough, K.M.1
Moran, W.J.2
Raubo, P.3
Harrity, J.P.A.4
-
36
-
-
10844243944
-
-
(b) Bose, G.; Nguyen, V. T. H.; Ullah, E.; Lahiri, S.; Görls, H.; Langer, P. J. Org. Chem. 2004, 69, 9128.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 9128
-
-
Bose, G.1
Nguyen, V.T.H.2
Ullah, E.3
Lahiri, S.4
Görls, H.5
Langer, P.6
-
37
-
-
0041696518
-
-
(c) Abelman, M. M.; Curtis, J. K.; James, D. R. Tetrahedron Lett. 2003, 44, 6527.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 6527
-
-
Abelman, M.M.1
Curtis, J.K.2
James, D.R.3
-
38
-
-
0038441546
-
-
(d) Medley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 4286
-
-
Medley, S.J.1
Moran, W.J.2
Price, D.A.3
Harrity, J.P.A.4
-
39
-
-
4644248178
-
-
For leading references on intermolecular aza-[3 + 3], see: (a) Sydorenko, N.; Hsung R. P.; Darwish, O. S.; Hahn, J. M.; Liu, J. J. Org. Chem. 2004, 69, 6732.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6732
-
-
Sydorenko, N.1
Hsung, R.P.2
Darwish, O.S.3
Hahn, J.M.4
Liu, J.5
-
40
-
-
0037019536
-
-
(b) Sklenicka, H. M.; Hsung, R. P.; McLaughlin, M. J.; Wei, L.-L.; Gerasyuto, A. I.; Brennessel, W. W. J. Am. Chem. Soc. 2002, 124, 10435.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 10435
-
-
Sklenicka, H.M.1
Hsung, R.P.2
McLaughlin, M.J.3
Wei, L.-L.4
Gerasyuto, A.I.5
Brennessel, W.W.6
-
41
-
-
0037071942
-
-
(c) McLaughlin, M. J.; Hsung, R. P.; Cole, K. C.; Hahn, J. M.; Wang, J. Org. Lett. 2002, 4, 2017.
-
(2002)
Org. Lett.
, vol.4
, pp. 2017
-
-
McLaughlin, M.J.1
Hsung, R.P.2
Cole, K.C.3
Hahn, J.M.4
Wang, J.5
-
42
-
-
0001703383
-
-
(d) Wei, L.-L.; Hsung, R. P.; Xiong, H.; Mulder, J. A.; Nkansah, N. T. Org. Lett. 1999, 1, 2145.
-
(1999)
Org. Lett.
, vol.1
, pp. 2145
-
-
Wei, L.-L.1
Hsung, R.P.2
Xiong, H.3
Mulder, J.A.4
Nkansah, N.T.5
-
43
-
-
0035901688
-
-
For intramolecular aza-[3 + 3], see: (a) Wei, L.-L.; Sklenicka, H. M.; Gerasyuto, A. I.; Hsung, R. P. Angew. Chem., Int. Ed. 2001, 40, 1516.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 1516
-
-
Wei, L.-L.1
Sklenicka, H.M.2
Gerasyuto, A.I.3
Hsung, R.P.4
-
44
-
-
19544385954
-
-
(b) Gerasyuto, A. I.; Hsung, R. P.; Sydorenko, N.; Slafer, B. W. J. Org. Chem. 2005, 70, 4248.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 4248
-
-
Gerasyuto, A.I.1
Hsung, R.P.2
Sydorenko, N.3
Slafer, B.W.4
-
45
-
-
20844437545
-
-
For some simple applications, see: (c) Sydorenko, N.; Zificsak, C. A.; Gerasyuto, A. I.; Hsung, R. P. Organic Biomol. Chem. 2005, 3, 2140.
-
(2005)
Organic Biomol. Chem.
, vol.3
, pp. 2140
-
-
Sydorenko, N.1
Zificsak, C.A.2
Gerasyuto, A.I.3
Hsung, R.P.4
-
46
-
-
0348041988
-
-
(d) Luo, S.; Zificsak, C. Z.; Hsung, R. P. Org. Lett. 2003, 5, 4709.
-
(2003)
Org. Lett.
, vol.5
, pp. 4709
-
-
Luo, S.1
Zificsak, C.Z.2
Hsung, R.P.3
-
48
-
-
0028205262
-
-
(b) McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. Synthesis 1994, 31.
-
(1994)
Synthesis
, pp. 31
-
-
McKillop, A.1
Taylor, R.J.K.2
Watson, R.J.3
Lewis, N.J.4
-
49
-
-
84947151032
-
-
Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
-
(1981)
Synth. Commun.
, vol.11
, pp. 513
-
-
Miyaura, N.1
Yanagi, T.2
Suzuki, A.3
-
50
-
-
33644757276
-
-
note
-
See the Supporting Information.
-
-
-
-
52
-
-
33644777138
-
-
note
-
Although we did not rigorously assign the relative stereochemistry at C4 and C5, we believed that NCS should have approached from the less hindered bottom face as observed in the hydrogenation of 27 that gave i in 90% yield as a single diastereomer. The relative stereochemistry C4 and C5 is unambiguous on the basis of coupling constants obtained for H4a and H4b. (Diagram presented)
-
-
-
-
53
-
-
33644770824
-
-
note
-
The deprotection was carried out earlier than expected because we could not do anything with 33 in completing the total synthesis.
-
-
-
-
54
-
-
33644769788
-
-
note
-
8.
-
-
-
-
57
-
-
0342306428
-
-
(c) Crabtree, R. H.; Felkin, H.; Fellebeen-Khan, T.; Morris, G. E. J. Organomet. Chem. 1979, 168, 183.
-
(1979)
J. Organomet. Chem.
, vol.168
, pp. 183
-
-
Crabtree, R.H.1
Felkin, H.2
Fellebeen-Khan, T.3
Morris, G.E.4
-
60
-
-
33644756199
-
-
note
-
2) (see ref 10b).
-
-
-
|