-
1
-
-
0026571746
-
-
Elsley, D. A.; MacLeod, D.; Miller, J. A.; Quayle, P.; Davies, G. M. Tetrahedron Lett. 1992, 33, 409.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 409
-
-
Elsley, D.A.1
MacLeod, D.2
Miller, J.A.3
Quayle, P.4
Davies, G.M.5
-
4
-
-
22744442306
-
-
For recent reviews, see: (a) Nicolaou, K. C.; Bulger, P. C.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4442.
-
(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 4442
-
-
Nicolaou, K.C.1
Bulger, P.C.2
Sarlah, D.3
-
6
-
-
27744536067
-
-
Conway, J. C.; Quayle, P.; Regan, A. C.; Urch, C. J. Tetrahedron 2005, 61, 11910.
-
(2005)
Tetrahedron
, vol.61
, pp. 11910
-
-
Conway, J.C.1
Quayle, P.2
Regan, A.C.3
Urch, C.J.4
-
8
-
-
15444363491
-
-
(b) For a recent application, see: Dias, L. C.; de Oliveira, L. G.; Vilcachagua, J. D.; Nigsch, F. J. Org. Chem. 2005, 70, 2225.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 2225
-
-
Dias, L.C.1
De Oliveira, L.G.2
Vilcachagua, J.D.3
Nigsch, F.4
-
9
-
-
67650676563
-
-
Abas, A.; Beddoes, R. L.; Conway, J. C.; Quayle, P.; Urch, C. J. Synlett 1995, 1264.
-
(1995)
Synlett
, pp. 1264
-
-
Abas, A.1
Beddoes, R.L.2
Conway, J.C.3
Quayle, P.4
Urch, C.J.5
-
10
-
-
27744440018
-
-
and references cited therein
-
(a) Helliwell, M.; Karim, S.; Parmee, E. R.; Thomas, E. J. Org. Biomol. Chem. 2005, 3, 3636; and references cited therein.
-
(2005)
Org. Biomol. Chem.
, vol.3
, pp. 3636
-
-
Helliwell, M.1
Karim, S.2
Parmee, E.R.3
Thomas, E.J.4
-
11
-
-
0031273440
-
-
For pertinent reviews, see: (b) Ikeda, H.; Omura, S. Chem. Rev. 1997, 97, 2591.
-
(1997)
Chem. Rev.
, vol.97
, pp. 2591
-
-
Ikeda, H.1
Omura, S.2
-
12
-
-
85013539395
-
-
Lindberg, T., Ed.; Academic Press: London
-
(c) Ley, S. V.; Armstrong, A. In Strategies and Tactics in Organic Synthesis Vol. 3; Lindberg, T., Ed.; Academic Press: London, 1991, 237.
-
(1991)
Strategies and Tactics in Organic Synthesis
, vol.3
, pp. 237
-
-
Ley, S.V.1
Armstrong, A.2
-
16
-
-
0030894227
-
-
For related rearrangements, see: Paquette, L. A.; Kinney, M. J.; Dullweber, U. J. Org. Chem. 1997, 62, 1713.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 1713
-
-
Paquette, L.A.1
Kinney, M.J.2
Dullweber, U.3
-
17
-
-
0000234345
-
-
For intermolecular etherification processes, see: (a) Bolitt, V.; Mioskowski, C.; Le, S.-G.; Falck, J. R. J. Org. Chem. 1990, 55, 5812.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 5812
-
-
Bolitt, V.1
Mioskowski, C.2
Le, S.-G.3
Falck, J.R.4
-
18
-
-
4544234925
-
-
(b) Jaunzems, J.; Kashin, D.; Schönberger, A.; Kirschning, A. Eur. J. Org. Chem. 2004, 3435.
-
(2004)
Eur. J. Org. Chem.
, pp. 3435
-
-
Jaunzems, J.1
Kashin, D.2
Schönberger, A.3
Kirschning, A.4
-
19
-
-
20544450144
-
-
(c) Lin, H.-C.; Du, W.-P.; Chang, C.-C.; Lin, C.-H. Tetrahedron Lett. 2005, 46, 5071.
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 5071
-
-
Lin, H.-C.1
Du, W.-P.2
Chang, C.-C.3
Lin, C.-H.4
-
21
-
-
0037189130
-
-
(a) This intermediate has been prepared previously, see: Sellès, P.; Lett, R. Tetrahedron Lett. 2002, 43, 4621.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 4621
-
-
Sellès, P.1
Lett, R.2
-
22
-
-
3242735104
-
-
(b) For a synthesis of racemic 10, see ref. 5b. Alcohol 14 has been prepared previously, see: Muñoz, D. M.; Passey, S. C.; Simpson, T. J.; Willis, C. L.; Campbell, J. B.; Rosser, R. Aust. J. Chem. 2004, 57, 645.
-
(2004)
Aust. J. Chem.
, vol.57
, pp. 645
-
-
Muñoz, D.M.1
Passey, S.C.2
Simpson, T.J.3
Willis, C.L.4
Campbell, J.B.5
Rosser, R.6
-
25
-
-
0028041228
-
-
(c) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262.
-
(1994)
Can. J. Chem.
, vol.72
, pp. 1262
-
-
Friesen, R.W.1
Loo, R.W.2
Sturino, C.F.3
-
28
-
-
12944327369
-
-
For carbonylative Stille reactions, see: (f) Steunenberg, P.; Jeanneret, V.; Zhu, Y.-H.; Vogel, P. Tetrahedron: Asymmetry 2005, 16, 337.
-
(2005)
Tetrahedron: Asymmetry
, vol.16
, pp. 337
-
-
Steunenberg, P.1
Jeanneret, V.2
Zhu, Y.-H.3
Vogel, P.4
-
30
-
-
0028041228
-
-
(h) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262.
-
(1994)
Can. J. Chem.
, vol.72
, pp. 1262
-
-
Friesen, R.W.1
Loo, R.W.2
Sturino, C.F.3
-
32
-
-
0141854965
-
-
(j) For the Pd-catalyzed coupling reactions of glucal-derived indium reagents, see: Lehmann, Y.; Awasthi, S.; Minehan, T. Org. Lett. 2003, 5, 2405-2408.
-
(2003)
Org. Lett.
, vol.5
, pp. 2405-2408
-
-
Lehmann, Y.1
Awasthi, S.2
Minehan, T.3
-
33
-
-
0000021944
-
-
For Stille-type cross-coupling reactions of iodoglucals, see: (k) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 4821
-
-
Friesen, R.W.1
Loo, R.W.2
-
37
-
-
49249149027
-
-
Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. A.; Roberts, S. M. Tetrahedron Lett. 1979, 20, 3981.
-
(1979)
Tetrahedron Lett.
, vol.20
, pp. 3981
-
-
Newton, R.F.1
Reynolds, D.P.2
Finch, M.A.W.3
Kelly, D.A.4
Roberts, S.M.5
-
38
-
-
28044453908
-
-
For reviews, see: (a) Negishi, E.-i.; Hu, Q.; Huang, Z.; Qian, M.; Wang, G. Aldrichimica Acta 2005, 38, 71.
-
(2005)
Aldrichimica Acta
, vol.38
, pp. 71
-
-
Negishi, E.-I.1
Hu, Q.2
Huang, Z.3
Qian, M.4
Wang, G.5
-
39
-
-
24144492430
-
-
de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim
-
(b) Negishi, E.-i.; Zeng, X.; Tan, Z.; Mingxing, Q.; Hu, Q.; Huang, Z. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Vol. 2; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004, 815.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
, vol.2
, pp. 815
-
-
Negishi, E.-I.1
Zeng, X.2
Tan, Z.3
Mingxing, Q.4
Hu, Q.5
In, H.Z.6
-
40
-
-
0142123938
-
-
For the use of Negishi cross-coupling reactions in related contexts, see: (c) Boucard, V.; Larrieu, K.; Lubin-Germain, N.; Uziel, J.; Auge, J. Synlett 2003, 1834.
-
(2003)
Synlett
, pp. 1834
-
-
Boucard, V.1
Larrieu, K.2
Lubin-Germain, N.3
Uziel, J.4
Auge, J.5
-
43
-
-
0025176058
-
-
(f) Tius, M. A.; Gu, X.-Q.; Gomez-Galeno, J. J. Am. Chem. Soc. 1990, 112, 8188.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 8188
-
-
Tius, M.A.1
Gu, X.-Q.2
Gomez-Galeno, J.3
-
44
-
-
0025819975
-
-
Confer: Boeckman, R. K.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1991, 113, 5337.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 5337
-
-
Boeckman, R.K.1
Charette, A.B.2
Asberom, T.3
Johnston, B.H.4
-
45
-
-
33645418464
-
-
note
-
2O quenching experiments.
-
-
-
-
46
-
-
33645408270
-
-
note
-
80Se: 656.2041. Found: 656.2042.
-
-
-
-
48
-
-
33645382144
-
-
Confer ref. 22b
-
Confer ref. 22b.
-
-
-
-
49
-
-
37049111829
-
-
(a) Jaurand, G.; Beau, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1981, 572.
-
(1981)
J. Chem. Soc., Chem. Commun.
, pp. 572
-
-
Jaurand, G.1
Beau, J.-M.2
Sinaÿ, P.3
-
50
-
-
0025289977
-
-
(b) Diez-Martin, D.; Grice, P.; Kolb, H. C.; Ley, S. V.; Madin, A. Tetrahedron Lett. 1990, 31, 3445.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 3445
-
-
Diez-Martin, D.1
Grice, P.2
Kolb, H.C.3
Ley, S.V.4
Madin, A.5
-
51
-
-
26444612098
-
-
(c) For related oxidative spirocyclization reactions, see: Potuzak, J. S.; Moilanen, S. B.; Tan, D. S. J. Am. Chem. Soc. 2005, 127, 13706.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 13706
-
-
Potuzak, J.S.1
Moilanen, S.B.2
Tan, D.S.3
-
52
-
-
0030792114
-
-
For an in-depth analysis, see: (a) Roush, W. R.; Sebesta, D. P.; Bennett, C. E. Tetrahedron 1997, 53, 8825.
-
(1997)
Tetrahedron
, vol.53
, pp. 8825
-
-
Roush, W.R.1
Sebesta, D.P.2
Bennett, C.E.3
-
53
-
-
0344196899
-
-
(b) Predojević, J.; Vukićević, M. D.; Wurst, K.; Onganania, K.-H.; Laus, G.; Vukićević, R. D. Carbohydr. Res. 2004, 339, 37; for structural studies.
-
(2004)
Carbohydr. Res.
, vol.339
, pp. 37
-
-
Predojević, J.1
Vukićević, M.D.2
Wurst, K.3
Onganania, K.-H.4
Laus, G.5
Vukićević, R.D.6
-
54
-
-
26844495248
-
-
For other approaches to the synthesis of 'contra-thermodynamic' spiroketals, see: (a) Doubskÿ Zedník, J.; Vašíč ková, S.; Koutek, B. Tetrahedron Lett. 2005, 46, 7923.
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 7923
-
-
Doubskÿ Zedník, J.1
Vašíčková, S.2
Koutek, B.3
-
55
-
-
22744450490
-
-
(b) Paterson, I.; Coster, M. J.; Chen, D. Y.-K.; Gibson, K. R.; Wallace, D. J. Org. Biomol. Chem. 2005, 2410.
-
(2005)
Org. Biomol. Chem.
, pp. 2410
-
-
Paterson, I.1
Coster, M.J.2
Chen, D.Y.-K.3
Gibson, K.R.4
Wallace, D.J.5
-
56
-
-
12944312239
-
-
(c) Takaoka, L. R.; Buckmelter, A. J.; LaCruz, T. E.; Rychnovsky, S. D. J. Am. Chem. Soc. 2005, 127, 528.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 528
-
-
Takaoka, L.R.1
Buckmelter, A.J.2
Lacruz, T.E.3
Rychnovsky, S.D.4
-
57
-
-
0028957654
-
-
(d) Chen, J.; Fletcher, M. T.; Kitching, W. Tetrahedron: Asymmetry 1995, 6, 967.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 967
-
-
Chen, J.1
Fletcher, M.T.2
Kitching, W.3
-
58
-
-
0037034916
-
-
(a) Milne, J. E.; Jarowicki, K.; Kocienski, P. J.; Alonso, J. Chem. Commun. 2002, 426.
-
(2002)
Chem. Commun.
, pp. 426
-
-
Milne, J.E.1
Jarowicki, K.2
Kocienski, P.J.3
Alonso, J.4
-
60
-
-
33645423132
-
-
note
-
(c) This route promises to provide access to substrates such as 3 with greater efficiency than observed using Beau's methodology. Beau's route (that used in this study, see ref. 14b) requires recycling of i in order to achieve the throughput required for preparative-scale reactions (Scheme 6).
-
-
-
|