-
2
-
-
0035078681
-
-
a) M. R. Boyd, C. Farina, P. Belfiore, S. Gagliardi, J. W. Kim, Y. Hayakawa, J. A. Beutler, T. C. McKee, B. J. Bowman, E. J. Bowman, J. Pharmacol. Exp. Ther. 2001, 297, 114;
-
(2001)
J. Pharmacol. Exp. Ther.
, vol.297
, pp. 114
-
-
Boyd, M.R.1
Farina, C.2
Belfiore, P.3
Gagliardi, S.4
Kim, J.W.5
Hayakawa, Y.6
Beutler, J.A.7
McKee, T.C.8
Bowman, B.J.9
Bowman, E.J.10
-
3
-
-
0345134728
-
-
b) for a recent review of syntheses and SAR studies, see: L. Yet, Chem. Rev. 2003, 103, 4283.
-
(2003)
Chem. Rev.
, vol.103
, pp. 4283
-
-
Yet, L.1
-
4
-
-
0001087954
-
-
J. W. Kim, K. Shin-ya, K. Furihata, Y. Hayakawa, H. Seto, J. Org. Chem. 1999, 64, 153.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 153
-
-
Kim, J.W.1
Shin-Ya, K.2
Furihata, K.3
Hayakawa, Y.4
Seto, H.5
-
5
-
-
0345359588
-
-
a) Y. Hayakawa, T. Tomikawa, K. Shin-Ya, N. Arao, K. Nagai, K-I. Suzuki, J. Antibiot. 2003, 56, 899;
-
(2003)
J. Antibiot.
, vol.56
, pp. 899
-
-
Hayakawa, Y.1
Tomikawa, T.2
Shin-Ya, K.3
Arao, N.4
Nagai, K.5
Suzuki, K.-I.6
-
6
-
-
0344497093
-
-
b) Y. Hayakawa, T. Tomikawa, K. Shin-Ya, N. Arao, K. Nagai, K-I. Suzuki, K. Furihata, J. Antibiot. 2003, 56, 905.
-
(2003)
J. Antibiot.
, vol.56
, pp. 905
-
-
Hayakawa, Y.1
Tomikawa, T.2
Shin-Ya, K.3
Arao, N.4
Nagai, K.5
Suzuki, K.-I.6
Furihata, K.7
-
7
-
-
0037613530
-
-
For the total synthesis of oximidine II, see: a) X. Wang, J. A. Porco, Jr, J. Am. Chem. Soc. 2003, 125, 6040;
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 6040
-
-
Wang, X.1
Porco Jr., J.A.2
-
8
-
-
0347286690
-
-
for recent studies on the synthesis of the oximidines, see: b) T. Haack, S. Kurtkaya, J. P. Snyder, G. I. Georg, Org. Lett. 2003, 5, 5019;
-
(2003)
Org. Lett.
, vol.5
, pp. 5019
-
-
Haack, T.1
Kurtkaya, S.2
Snyder, J.P.3
Georg, G.I.4
-
9
-
-
0041508391
-
-
c) J. E. Harvey, S. A. Raw, R. J. K. Taylor, Tetrahedron Lett. 2003, 44, 7209.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 7209
-
-
Harvey, J.E.1
Raw, S.A.2
Taylor, R.J.K.3
-
11
-
-
0038202225
-
-
b) R. Shen, C. T. Lin, E. J. Bowman, B. J. Bowman, J. A. Porco, Jr, J. Am. Chem. Soc. 2003, 125, 7889;
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 7889
-
-
Shen, R.1
Lin, C.T.2
Bowman, E.J.3
Bowman, B.J.4
Porco Jr., J.A.5
-
12
-
-
0035905656
-
-
for applications of this method, see: ref. [5a] and c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5286;
-
(2001)
Chem. Eur. J.
, vol.7
, pp. 5286
-
-
Fürstner, A.1
Dierkes, T.2
Thiel, O.R.3
Blanda, G.4
-
13
-
-
0037157091
-
-
d) R. Shen, C. T. Lin, J. A. Porco, Jr, J. Am. Chem. Soc. 2002, 124, 5650;
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 5650
-
-
Shen, R.1
Lin, C.T.2
Porco Jr., J.A.3
-
14
-
-
0346099320
-
-
e) K. C. Nicolaou, D. W. Kim, R. Baati, A. O'Brate, P. Giannakakou, Chem. Eur. J. 2003, 9, 6177;
-
(2003)
Chem. Eur. J.
, vol.9
, pp. 6177
-
-
Nicolaou, K.C.1
Kim, D.W.2
Baati, R.3
O'Brate, A.4
Giannakakou, P.5
-
17
-
-
0000785058
-
-
Recent reviews: a) A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012;
-
(2000)
Angew. Chem.
, vol.112
, pp. 3140
-
-
Fürstner, A.1
-
18
-
-
0001399412
-
-
Recent reviews: a) A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012;
-
(2000)
Angew. Chem. Int. Ed.
, vol.39
, pp. 3012
-
-
-
20
-
-
0037436934
-
-
c) for RCM with a vinyl epoxide, see: K. Yamamoto, K. Biswas, C. Gaul, S. J. Danishefsky, Tetrahedron Lett. 2003, 44, 3297.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 3297
-
-
Yamamoto, K.1
Biswas, K.2
Gaul, C.3
Danishefsky, S.J.4
-
21
-
-
0037012401
-
-
Y. Wu, X. Liao, R. Wang, X.-S. Xie, J. K. De Brabander, J. Am. Chem. Soc. 2002, 124, 3245.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 3245
-
-
Wu, Y.1
Liao, X.2
Wang, R.3
Xie, X.-S.4
De Brabander, J.K.5
-
22
-
-
0033533652
-
-
For an example of allylic substitution effects on reaction rates of RCM, see: T. R. Hoye, H. Zhao, Org. Lett. 1999, 1, 1123.
-
(1999)
Org. Lett.
, vol.1
, pp. 1123
-
-
Hoye, T.R.1
Zhao, H.2
-
23
-
-
7644220480
-
-
(New York, NY), ORGN-670
-
For studies regarding relay RCM, see: a) T. R. Hoye, J. Wang, 226th ACS National Meeting (New York, NY), 2003, ORGN-670;
-
(2003)
226th ACS National Meeting
-
-
Hoye, T.R.1
Wang, J.2
-
24
-
-
4544303715
-
-
(New Orleans, LA), ORGN-620
-
b) T. R. Hoye, R. Thomas, H. Zhao, 218th ACS National Meeting, (New Orleans, LA), 1999, ORGN-620;
-
(1999)
218th ACS National Meeting
-
-
Hoye, T.R.1
Thomas, R.2
Zhao, H.3
-
26
-
-
0030857814
-
-
d) for another application of a "relay" entity in the assembly of reacting sites in RCM, see: A. Fürstner, K. Langemann, Synthesis 1997, 792.
-
(1997)
Synthesis
, pp. 792
-
-
Fürstner, A.1
Langemann, K.2
-
27
-
-
0037138704
-
-
The chiral nonracemic epoxide 16 was prepared by hydrolytic kinetic resolution of the racemic epoxide (48% yield, 95% ee): S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 1307
-
-
Schaus, S.E.1
Brandes, B.D.2
Larrow, J.F.3
Tokunaga, M.4
Hansen, K.B.5
Gould, A.E.6
Furrow, M.E.7
Jacobsen, E.N.8
-
29
-
-
4544265781
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note
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Use of a sterically demanding TBS protecting group on the secondary alcohol resulted in low diastereoselectivity of the Sharpless asymmetric epoxidation (4:1).
-
-
-
-
31
-
-
0001617316
-
-
J. W. Labadie, D. Tueting, J. K. Stille, J. Org. Chem. 1983, 48, 4634.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 4634
-
-
Labadie, J.W.1
Tueting, D.2
Stille, J.K.3
-
32
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-
4544273147
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note
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Use of the Grubbs first-generation catalyst led to the corresponding by-products 6 (Scheme 2).
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-
33
-
-
0034734340
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-
S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8168
-
-
Garber, S.B.1
Kingsbury, J.S.2
Gray, B.L.3
Hoveyda, A.H.4
-
34
-
-
4544282270
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-
P. R. Blakemore, W. J. Cole, P. J. Kociénski, A Morley, Synthesis 1996, 285. For the preparation of 25, see the Supporting Information.
-
(1996)
Synthesis
, pp. 285
-
-
Blakemore, P.R.1
Cole, W.J.2
Kociénski, P.J.3
Morley, A.4
-
35
-
-
33845373603
-
-
K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 7408
-
-
Takai, K.1
Nitta, K.2
Utimoto, K.3
-
36
-
-
33947293559
-
-
a) D. Seyferth, R. S. Marmor, P. Hilbert, J. Org. Chem. 1971, 36, 1379;
-
(1971)
J. Org. Chem.
, vol.36
, pp. 1379
-
-
Seyferth, D.1
Marmor, R.S.2
Hilbert, P.3
-
39
-
-
0001517035
-
-
d) D. G. Brown, E. J. Velthuisen, J. R. Commerford, R. G. Brisbois, T. R. Hoye, J. Org. Chem. 1996, 61, 2540.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 2540
-
-
Brown, D.G.1
Velthuisen, E.J.2
Commerford, J.R.3
Brisbois, R.G.4
Hoye, T.R.5
-
40
-
-
0000355152
-
-
For the preparation of 30, see the Supporting Information; a) for a related chloromethyl benzothiazole sulfone reagent, see: J. B. Baudin, G. Hareau, S. A. Julia, R. Lorne, O. Ruel, Bull. Soc. Chim. Fr. 1993, 130, 856;
-
(1993)
Bull. Soc. Chim. Fr.
, vol.130
, pp. 856
-
-
Baudin, J.B.1
Hareau, G.2
Julia, S.A.3
Lorne, R.4
Ruel, O.5
-
42
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4544351423
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note
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1H NMR analysis.
-
-
-
-
43
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4544284526
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note
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In our synthesis of oximidine II (ref. [5a]), we utilized a silylated phenol substrate treated with base and amide (2 equiv each) in a copper-mediated coupling to effect both silyl ether deprotection and enamide formation. However, use of excess base and amide in the syntheses described herein led to significant decomposition of the sensitive vinyl epoxide moiety.
-
-
-
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44
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4544278387
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note
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V-ATPase activity was determined as described in the Supporting Information.
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