-
1
-
-
0000670453
-
-
Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 361
-
-
Satake, M.1
Murata, M.2
Yasumoto, T.3
-
2
-
-
0032890443
-
-
Morohashi, A.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1999, 40, 97.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 97
-
-
Morohashi, A.1
Satake, M.2
Yasumoto, T.3
-
4
-
-
0034804021
-
-
(b) Kadota, I.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 6702.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 6702
-
-
Kadota, I.1
Ohno, A.2
Matsuda, K.3
Yamamoto, Y.4
-
5
-
-
0037017775
-
-
(c) Marmsater, F. P.; Vanecko, J. A.; West, F. G. Tetrahedron 2002, 58, 2027.
-
(2002)
Tetrahedron
, vol.58
, pp. 2027
-
-
Marmsater, F.P.1
Vanecko, J.A.2
West, F.G.3
-
6
-
-
0037051647
-
-
(d) Kadota, I.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 3562.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 3562
-
-
Kadota, I.1
Ohno, A.2
Matsuda, K.3
Yamamoto, Y.4
-
8
-
-
0037132628
-
-
(a) Fuwa, H.; Kainuma, N.; Tachibana, K.; Sasaki, M. J. Am. Chem. Soc. 2002, 124, 14983.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 14983
-
-
Fuwa, H.1
Kainuma, N.2
Tachibana, K.3
Sasaki, M.4
-
9
-
-
0037425560
-
-
(b) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 46
-
-
Kadota, I.1
Takamura, H.2
Sato, K.3
Ohno, A.4
Matsuda, K.5
Yamamoto, Y.6
-
10
-
-
0002521312
-
-
Bertozzi, C., Wang, P. G., Eds.; Marcel Dekker: New York
-
For a recent monograph on C-glycoside synthesis, see: Postema, M. H. D. In Glycochemistry Principles, Synthesis and Applications; Bertozzi, C., Wang, P. G., Eds.; Marcel Dekker: New York, 2000; pp 77-131.
-
(2000)
Glycochemistry Principles, Synthesis and Applications
, pp. 77-131
-
-
Postema, M.H.D.1
-
13
-
-
0037017749
-
-
(c) Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron 2002, 58, 1997.
-
(2002)
Tetrahedron
, vol.58
, pp. 1997
-
-
Allwein, S.P.1
Cox, J.M.2
Howard, B.E.3
Johnson, H.W.B.4
Rainier, J.D.5
-
14
-
-
0037175485
-
-
Among the more challenging structural features of gambierol are the C(7), C(11), C(21), and C(23) stereocenters. These centers contain angular methyl groups oriented in a 1,3-disposition to one another and, for our approach, require the addition of a carbon nucleophile to the more substituted end of a trisubstituted glycal anhydride. For synthetic work by others toward these centers, see refs 3 and 4 and: Suzuki, K.; Matsukura, H.; Matsuo, G.; Koshino, H.; Nakata, T. Tetrahedron Lett. 2002, 43, 8653.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 8653
-
-
Suzuki, K.1
Matsukura, H.2
Matsuo, G.3
Koshino, H.4
Nakata, T.5
-
17
-
-
0011674952
-
-
Lesimple, P.; Beau, J.-M.; Jaurand, G.; Sinay, P. Tetrahedron Lett. 1986, 27, 6201.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 6201
-
-
Lesimple, P.1
Beau, J.-M.2
Jaurand, G.3
Sinay, P.4
-
18
-
-
84985666791
-
-
For the preparation of DMDO, see: Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
-
(1991)
Chem. Ber.
, vol.124
, pp. 2377
-
-
Adam, W.1
Bialas, J.2
Hadjiarapoglou, L.3
-
19
-
-
0029978637
-
-
To obtain reproducible yields on a large scale, we used Messeguer's "acetone-free" conditions. The use of this protocol allowed us to avoid the concentration of the epoxide. See the Experimental Section and: Ferrer, M.; Gibert, M.; Sánchez-Baeza, F.; Messeguer, A. Tetrahedron Lett. 1996, 37, 3585.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 3585
-
-
Ferrer, M.1
Gibert, M.2
Sánchez-Baeza, F.3
Messeguer, A.4
-
20
-
-
0141485878
-
-
note
-
Our previous work with similarly substituted epoxides had resulted in poor diastereoselectivity and/or low yields. The major products from these reactions were generally rationalized as coming from the formation of intermediate oxocarbenium ions. See refs 6 and 8.
-
-
-
-
21
-
-
0141597527
-
-
note
-
We have also coupled Al nucleophiles with trisubstituted glycal anhydrides. See refs 6b and 6c.
-
-
-
-
22
-
-
0000498386
-
-
For selected examples of enol ether-olefin RCM, see: (a) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029. (b) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (c) Postema, M. H. D. J. Org. Chem. 1999, 64, 1770. (d) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372. (e) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (f) Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 4029
-
-
Fujimura, O.1
Fu, G.C.2
Grubbs, R.H.3
-
23
-
-
0031031774
-
-
For selected examples of enol ether-olefin RCM, see: (a) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029. (b) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (c) Postema, M. H. D. J. Org. Chem. 1999, 64, 1770. (d) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372. (e) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (f) Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 123
-
-
Clark, J.S.1
Kettle, J.G.2
-
24
-
-
0033583130
-
-
For selected examples of enol ether-olefin RCM, see: (a) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029. (b) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (c) Postema, M. H. D. J. Org. Chem. 1999, 64, 1770. (d) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372. (e) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (f) Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1770
-
-
Postema, M.H.D.1
-
25
-
-
0034677109
-
-
For selected examples of enol ether-olefin RCM, see: (a) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029. (b) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (c) Postema, M. H. D. J. Org. Chem. 1999, 64, 1770. (d) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372. (e) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (f) Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179.
-
(2000)
Angew. Chem. Int. Ed.
, vol.39
, pp. 372
-
-
Clark, J.S.1
Hamelin, O.2
-
26
-
-
0034685462
-
-
For selected examples of enol ether-olefin RCM, see: (a) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029. (b) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (c) Postema, M. H. D. J. Org. Chem. 1999, 64, 1770. (d) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372. (e) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (f) Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 3783
-
-
Chatterjee, A.K.1
Morgan, J.P.2
Scholl, M.3
Grubbs, R.H.4
-
27
-
-
0035825039
-
-
For selected examples of enol ether-olefin RCM, see: (a) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029. (b) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (c) Postema, M. H. D. J. Org. Chem. 1999, 64, 1770. (d) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372. (e) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. (f) Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 179
-
-
Rainier, J.D.1
Cox, J.M.2
Allwein, S.P.3
-
28
-
-
0141709214
-
-
Ph.D. Dissertation, The University of Arizona, Tucson, Arizona
-
To the best of our knowledge, the only other example of the formation of a tetrasubstituted enol ether using metathesis also came from our laboratory. See: Cox, J. M. Ph.D. Dissertation, The University of Arizona, Tucson, Arizona, 2002.
-
(2002)
-
-
Cox, J.M.1
-
29
-
-
33751158544
-
-
Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 2668
-
-
Takai, K.1
Kakiuchi, T.2
Kataoka, Y.3
Utimoto, K.4
-
30
-
-
0141597526
-
-
note
-
Other enol ether-forming protocols (Tebbe, Petasis) were even less successful in our hands.
-
-
-
-
31
-
-
0001077422
-
-
Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. B. J. Am. Chem. Soc. 1990, 112, 3875.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 3875
-
-
Schrock, R.R.1
Murdzek, J.S.2
Bazan, G.C.3
Robbins, J.4
DiMare, M.5
O'Regan, M.B.6
-
32
-
-
0033598258
-
-
Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
-
(1999)
Org. Lett.
, vol.1
, pp. 953
-
-
Scholl, M.1
Ding, S.2
Lee, C.W.3
Grubbs, R.H.4
-
33
-
-
0034814443
-
-
See ref 20 and: Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 6543
-
-
Sanford, M.S.1
Love, J.A.2
Grubbs, R.H.3
-
34
-
-
0000559010
-
-
We believe that there could be two reasons for the need for elevated temperatures: (1) the inherent difficulty associated with generating tetrasubstituted enol ethers; (2) the reaction may be proceeding through a relatively unreactive Fischer carbene intermediate prior to cyclization. For an excellent study on the formation and reactivity of Fischer carbenes from enol ethers and 14, see: Louie, J.; Grubbs, R. H. Organometallics 2002, 21, 2153.
-
(2002)
Organometallics
, vol.21
, pp. 2153
-
-
Louie, J.1
Grubbs, R.H.2
-
35
-
-
0025255550
-
-
Shekhani, M. S.; Khan, K. M.; Mahmood, K.; Shah, P. M.; Malik, S. Tetrahedron Lett. 1990, 31, 1669.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 1669
-
-
Shekhani, M.S.1
Khan, K.M.2
Mahmood, K.3
Shah, P.M.4
Malik, S.5
-
36
-
-
0141485876
-
-
note
-
Attempts to selectively remove the TBDPS group from 10 were unsuccessful.
-
-
-
-
38
-
-
0141820528
-
-
note
-
We also attempted to cyclize 17 using Schrock's catalyst 13 without success.
-
-
-
-
39
-
-
0033007618
-
-
Hydroboration of cyclic enol ethers has been applied to the synthesis of polycyclic ether natural products. For a selected example, see: Nicolaou, K. C. ; Bunnage, M. E.; McGarry, D. G.; Shi, S.; Somers, P. K.; Wallace, P. A.; Chu, X.-J.; Konstantinos, A.; A.; Gunzner, J. L.; Yang, Z. Chem. Eur. J. 1999, 5, 599.
-
(1999)
Chem. Eur. J.
, vol.5
, pp. 599
-
-
Nicolaou, K.C.1
Bunnage, M.E.2
McGarry, D.G.3
Shi, S.4
Somers, P.K.5
Wallace, P.A.6
Chu, X.-J.7
Konstantinos, A.A.8
Gunzner, J.L.9
Yang, Z.10
-
40
-
-
0033574384
-
-
For other examples of this transformation, see ref 8 and: Fujiwara, K.; Awakura, D.; Tsunashima, M.; Nakamura, A.; Honma, T.; Murai, A. J. Org. Chem. 1999, 64, 2616.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 2616
-
-
Fujiwara, K.1
Awakura, D.2
Tsunashima, M.3
Nakamura, A.4
Honma, T.5
Murai, A.6
-
41
-
-
0141485877
-
-
note
-
Minor product from this coupling is diastereomeric at C(20). We believe that this material comes from the direct reduction of 19.
-
-
-
-
42
-
-
0141820527
-
-
note
-
Another possibility would involve an RCM sequence. We have previously demonstrated the generation of oxepenes using RCM; see ref 6c.
-
-
-
-
43
-
-
0037151671
-
-
Winkler, J. D.; Rouse, M. B.; Greaney, M. F.; Harrison, S. J.; Jeon, Y. T. J. Am. Chem. Soc. 2002, 124, 9726.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 9726
-
-
Winkler, J.D.1
Rouse, M.B.2
Greaney, M.F.3
Harrison, S.J.4
Jeon, Y.T.5
|