-
1
-
-
0034607947
-
-
(a) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645-1680.
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 1645-1680
-
-
Asano, N.1
Nash, R.J.2
Molyneux, R.J.3
Fleet, G.W.J.4
-
3
-
-
0033549740
-
-
For a review of iminosugars, see: (a) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300-2324.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2300-2324
-
-
Sears, P.1
Wong, C.-H.2
-
6
-
-
0000904807
-
-
(d) Fellows, L. E.; Kite, G. C.; Nash, R. J.; Simmonds, M. S. J.; Scofield, A. M. Rec. Adv. Phytochem. 1989, 23, 395-427.
-
(1989)
Rec. Adv. Phytochem.
, vol.23
, pp. 395-427
-
-
Fellows, L.E.1
Kite, G.C.2
Nash, R.J.3
Simmonds, M.S.J.4
Scofield, A.M.5
-
7
-
-
0034721683
-
-
For a review of swainsonine syntheses, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579-8629.
-
(2000)
Tetrahedron
, vol.56
, pp. 8579-8629
-
-
Nemr, A.E.1
-
8
-
-
15444367790
-
-
For more recent syntheses, see: (b) Martin, R.; Murruzzu, C.; Pericas, M. A.; Riera, A. J. Org. Chem. 2005, 70, 2325-2328.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 2325-2328
-
-
Martin, R.1
Murruzzu, C.2
Pericas, M.A.3
Riera, A.4
-
9
-
-
10044237855
-
-
(c) Heimgaertner, G.; Raatz, D.; Reiser, O. Tetrahedron 2005, 61, 643-655.
-
(2005)
Tetrahedron
, vol.61
, pp. 643-655
-
-
Heimgaertner, G.1
Raatz, D.2
Reiser, O.3
-
10
-
-
5444267441
-
-
(d) Song, L.; Duesler, E. N.; Mariano, P. S. J. Org. Chem. 2004, 69, 7284-7293.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 7284-7293
-
-
Song, L.1
Duesler, E.N.2
Mariano, P.S.3
-
12
-
-
0037159762
-
-
(f) Pearson, W. H.; Ren, Y.; Powers, J. D. Heterocycles 2002, 58, 421-430.
-
(2002)
Heterocycles
, vol.58
, pp. 421-430
-
-
Pearson, W.H.1
Ren, Y.2
Powers, J.D.3
-
14
-
-
0037076936
-
-
(h) Buschmann, N.; Rueckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325-4329.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 4325-4329
-
-
Buschmann, N.1
Rueckert, A.2
Blechert, S.3
-
15
-
-
0035831144
-
-
(i) Zhao, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761-1767.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 1761-1767
-
-
Zhao, H.1
Hans, S.2
Cheng, X.3
Mootoo, D.R.4
-
16
-
-
0021269541
-
-
Ali, M. H.; Hough, L.; Richardson, A. C. J. Chem. Soc., Chem. Commun. 1984, 447-448.
-
(1984)
J. Chem. Soc., Chem. Commun.
, pp. 447-448
-
-
Ali, M.H.1
Hough, L.2
Richardson, A.C.3
-
17
-
-
0000448652
-
-
Fleet, G. W. J.; Gough, M. J.; Smith, P. W. Tetrahedron Lett. 1984, 25, 1853-1856.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 1853-1856
-
-
Fleet, G.W.J.1
Gough, M.J.2
Smith, P.W.3
-
19
-
-
0007208047
-
-
Adams, C. E.; Walker, F. J.; Sharpless, K. B. J. Org. Chem. 1985, 50, 420-422.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 420-422
-
-
Adams, C.E.1
Walker, F.J.2
Sharpless, K.B.3
-
20
-
-
0024553116
-
-
Bennett, R. B.; Choi, J. R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 2580-2582
-
-
Bennett, R.B.1
Choi, J.R.2
Montgomery, W.D.3
Cha, J.K.4
-
22
-
-
0038975186
-
-
(a) Oishi, T.; Iwakuma, T.; Hirama, M.; Ito, S. Synlett 1995, 404-406.
-
(1995)
Synlett
, pp. 404-406
-
-
Oishi, T.1
Iwakuma, T.2
Hirama, M.3
Ito, S.4
-
23
-
-
0030592842
-
-
(b) Davis, B.; Bell, A. A.; Nash, R. J.; Watson, A. A.; Griffiths, R. C.; Jones, M. G.; Smith, C.; Fleet, G. W. J. Tetrahedron Lett. 1996 37, 8565-8568.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 8565-8568
-
-
Davis, B.1
Bell, A.A.2
Nash, R.J.3
Watson, A.A.4
Griffiths, R.C.5
Jones, M.G.6
Smith, C.7
Fleet, G.W.J.8
-
24
-
-
0026317511
-
-
For the bioactivities of swainsonine, see: (a) Elbein, A. D. FASEB J. 1991, 5, 3055-3063.
-
(1991)
FASEB J.
, vol.5
, pp. 3055-3063
-
-
Elbein, A.D.1
-
25
-
-
33646454679
-
-
(b) Goss, P. E.; Reid, C. L.; Bailey, D.; Dennis, J. W. Clin. Cancer Res. 1997, 3, 11077-11086.
-
(1997)
Clin. Cancer Res.
, vol.3
, pp. 11077-11086
-
-
Goss, P.E.1
Reid, C.L.2
Bailey, D.3
Dennis, J.W.4
-
26
-
-
0028347285
-
-
(c) Galustian, C.; Foulds, S.; Dye, J. F.; Guillou, P. J. Immunopharmacol. 1994, 27, 165-172.
-
(1994)
Immunopharmacol.
, vol.27
, pp. 165-172
-
-
Galustian, C.1
Foulds, S.2
Dye, J.F.3
Guillou, P.J.4
-
27
-
-
0024781822
-
-
(d) Grzegorzewski, K.; Newton, S. A.; Akiyama, S. K.; Sharrow, S.; Olden, K.; White, S. L. Cancer Commun. 1989, 1, 373-279.
-
(1989)
Cancer Commun.
, vol.1
, pp. 373-1279
-
-
Grzegorzewski, K.1
Newton, S.A.2
Akiyama, S.K.3
Sharrow, S.4
Olden, K.5
White, S.L.6
-
29
-
-
0024539433
-
-
(f) Cenci Di Bello, I.; Fleet, G.; Namgoong, S. K.; Tadano, K.; Winchester, B. Biochem. J. 1989, 259, 855-861.
-
(1989)
Biochem. J.
, vol.259
, pp. 855-861
-
-
Cenci Di Bello, I.1
Fleet, G.2
Namgoong, S.K.3
Tadano, K.4
Winchester, B.5
-
31
-
-
0020469388
-
-
(h) Tulsiani, D. R. P.; Harris, T. M.; Touster, O. J. Biol. Chem. 1982, 257, 7936-7939.
-
(1982)
J. Biol. Chem.
, vol.257
, pp. 7936-7939
-
-
Tulsiani, D.R.P.1
Harris, T.M.2
Touster, O.3
-
32
-
-
0021972048
-
-
(i) Kino, T.; Inamura, N.; Nakahara, K.; Kiyoto, S.; Goto, T.; Terano, H.; Kohsaka, M. J. Antibiot. 1985, 38, 936-940.
-
(1985)
J. Antibiot.
, vol.38
, pp. 936-940
-
-
Kino, T.1
Inamura, N.2
Nakahara, K.3
Kiyoto, S.4
Goto, T.5
Terano, H.6
Kohsaka, M.7
-
33
-
-
0017494276
-
-
An Achmatowicz reaction is the oxidative rearrangement of furyl alcohols to 2-substituted 6-hydroxy-2H-pyran-3(6H)-ones; see: (a) Achmatowicz, O.; Bielski, R. Carbohydr. Res. 1977, 55, 165-176.
-
(1977)
Carbohydr. Res.
, vol.55
, pp. 165-176
-
-
Achmatowicz, O.1
Bielski, R.2
-
34
-
-
24944541990
-
-
and references therein
-
For its recent use in carbohydrate synthesis, see: (b) Guo, H.; O'Doherty, G. A. Org. Lett. 2005, 7, 3921-3924 and references therein.
-
(2005)
Org. Lett.
, vol.7
, pp. 3921-3924
-
-
Guo, H.1
O'Doherty, G.A.2
-
35
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33646447162
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note
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In the Fleet synthesis of swainsonine a similar reductive amination was employed; see ref 5.
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36
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33646454213
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note
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While we have prepared both D- and L-swainsonine, for simplicity herein we only show the L-enantiomer.
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37
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0347022328
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3N (1:1 instead of 2:1) was required for the Noyori reduction of compounds with primary TBS groups; see: Li, M.; Scott, J. G.; O'Doherty, G. A. Tetrahedron Lett. 2004, 45, 1005-1009.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 1005-1009
-
-
Li, M.1
Scott, J.G.2
O'Doherty, G.A.3
-
39
-
-
1642342224
-
-
(b) Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428-3429.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3428-3429
-
-
Babu, R.S.1
Zhou, M.2
O'Doherty, G.A.3
-
41
-
-
22544437286
-
-
de Oliveira, R. N.; Cottier, L.; Sinou, D.; Srivastava, R. M. Tetrahedron 2005, 61, 8271-8281.
-
(2005)
Tetrahedron
, vol.61
, pp. 8271-8281
-
-
De Oliveira, R.N.1
Cottier, L.2
Sinou, D.3
Srivastava, R.M.4
-
42
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25844446180
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Presumably, because of the rigid nature of the 7 and the equatorial nature of the allylic azide no [3,3] sigmatropic rearrangement was observed; see: Feldman, A. K.; Colasson, B.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 13444-13445.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 13444-13445
-
-
Feldman, A.K.1
Colasson, B.2
Sharpless, K.B.3
Fokin, V.V.4
-
43
-
-
0029746258
-
-
(a) Hudlicky, T.; Abboud, K. A.; Bolonick, J.; Maurya, R.; Stanton, M. L.; Thorpe, A. J. Chem. Commun. 1996, 1717-1718.
-
(1996)
Chem. Commun.
, pp. 1717-1718
-
-
Hudlicky, T.1
Abboud, K.A.2
Bolonick, J.3
Maurya, R.4
Stanton, M.L.5
Thorpe, A.J.6
-
44
-
-
0035833033
-
-
(b) Takao, K.-I.; Hara, M.; Tsujita, T.; Yoshida, K.-I.; Tadano, K.-I. Tetrahedron Lett. 2001, 42, 4665-4668.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 4665-4668
-
-
Takao, K.-I.1
Hara, M.2
Tsujita, T.3
Yoshida, K.-I.4
Tadano, K.-I.5
-
45
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33646439209
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note
-
By simply switching the (S,S)-Noyori reagent for the reduction of 10 to (ent)-9 to the (R,R)-Noyori reagent (10 to 9), D-swainsonine was prepared from 9 in nearly identical overall yield.
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