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Polyoxins and nikkomycins are not so effective as fungicidal agents when they are tested against whole cell cultures. See: (a) Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174- 180. (b) Bohem, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307-2314.
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For comprehensive reviews on synthesis of peptidyl nucleoside antibiotics and related compounds, see: (a) Knapp, S. Chem. Rev. 1995, 95, 1859-1876. (b) Garner, P. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Part A, Vol. 1, pp 397-434.
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For comprehensive reviews on synthesis of peptidyl nucleoside antibiotics and related compounds, see: (a) Knapp, S. Chem. Rev. 1995, 95, 1859-1876. (b) Garner, P. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Part A, Vol. 1, pp 397-434.
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For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891- 6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
-
(1999)
Eur. J. Org. Chem.
, pp. 1455-1458
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-
Caputo, R.1
Guaragna, A.2
Palumbo, G.3
Pedatella, S.4
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45
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0030899204
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-
For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891- 6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
-
(1997)
Drugs
, vol.53
, pp. 657-680
-
-
Perry, C.M.1
Faulds, D.2
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46
-
-
0033578086
-
-
For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891- 6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
-
(1999)
J. Med. Chem.
, vol.42
, pp. 2212-2217
-
-
Lin, J.-S.1
Kira, T.2
Gullen, E.3
Choi, Y.4
Qu, F.5
Chu, C.K.6
Cheng, Y.-C.7
-
47
-
-
0031986265
-
-
For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891- 6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
-
(1998)
Tetrahedron
, vol.54
, pp. 243-256
-
-
Mellor, B.J.1
Murray, P.E.2
Thomas, E.J.3
-
48
-
-
0030734550
-
-
For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891- 6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 7430-7434
-
-
Xiang, Y.1
Gi, H.-J.2
Niu, D.3
Schinazi, R.F.4
Zhao, K.5
-
49
-
-
0033534494
-
-
For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891- 6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 231-234
-
-
Hong, J.J.1
Gao, M.-Y.2
Chu, C.K.3
-
50
-
-
0032476077
-
-
For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891-6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 6891-6899
-
-
Yamada, K.1
Sakata, S.2
Yoshimura, Y.3
-
51
-
-
0029876396
-
-
For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891- 6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
-
(1996)
Nucleosides Nucleotides
, vol.15
, pp. 1113-1120
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-
Rassu, G.1
Zanardi, F.2
Cornia, M.3
Casiraghi, G.4
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52
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0032849660
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For representative examples, see: (oxothiolanyl) (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 1999, 1455-1458. (b) Perry, C. M.; Faulds, D. Drugs 1997, 53, 657-680. (dioxolanyl) (c) Lin, J.-S.; Kira, T.; Gullen, E.; Choi, Y.; Qu, F.; Chu, C. K.; Cheng, Y.-C. J. Med. Chem. 1999, 42, 2212-2217. (d) Mellor, B. J.; Murray, P. E.; Thomas, E. J. Tetrahedron 1998, 54, 243-256. (isoxazolidinyl) (e) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430-7434. (thiofuranosyl) (f) Hong, J. J.; Gao, M.-Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231-234. (g) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891- 6899. (thiazolidinyl) (h) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G. Nucleosides Nucleotides 1996, 15, 1113-1120. (pyrrolidinyl (aza)) (i) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541-1554.
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(1999)
Synthesis
, pp. 1541-1554
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Yokoyama, M.1
Momotake, A.2
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0034112410
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For recent accounts, see: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442-454. (b) Merino, P.; Tejero, T. Molecules 1999, 4, 165-175. (c) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. In Recent Research Developments in Synthetic Organic Chemistry; Pandalai, S. G., Ed.; Transworld Research Network: Trivandum, India, 1998; Vol. 1, pp 109-121.
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Synlett
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Merino, P.1
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54
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For recent accounts, see: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442-454. (b) Merino, P.; Tejero, T. Molecules 1999, 4, 165-175. (c) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. In Recent Research Developments in Synthetic Organic Chemistry; Pandalai, S. G., Ed.; Transworld Research Network: Trivandum, India, 1998; Vol. 1, pp 109-121.
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Pandalai, S. G., Ed.; Transworld Research Network: Trivandum, India
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For recent accounts, see: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442-454. (b) Merino, P.; Tejero, T. Molecules 1999, 4, 165-175. (c) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. In Recent Research Developments in Synthetic Organic Chemistry; Pandalai, S. G., Ed.; Transworld Research Network: Trivandum, India, 1998; Vol. 1, pp 109-121.
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56
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For a review, see: Pan, S.; Amankulor, N. M.; Zhao, K. Tetrahedron 1998, 54, 6587-6604.
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Merino, P.; Franco, S.; Garces, N.; Merchan, F. L.; Tejero, T. Chem. Commun. 1998, 493-494.
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58
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0001101886
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We have amply demonstrated that nucleophilic additions to nitrones derived from serine can be stereocontrolled by the appropriate choice of the protecting groups in the nitrone. See: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 5627-5630. (b) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646. (c) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813-1816.
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Merino, P.1
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59
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0032570493
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-
We have amply demonstrated that nucleophilic additions to nitrones derived from serine can be stereocontrolled by the appropriate choice of the protecting groups in the nitrone. See: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 5627- 5630. (b) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646. (c) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813-1816.
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Tetrahedron: Asymmetry
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Merino, P.1
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60
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0031562394
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We have amply demonstrated that nucleophilic additions to nitrones derived from serine can be stereocontrolled by the appropriate choice of the protecting groups in the nitrone. See: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 5627- 5630. (b) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646. (c) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813-1816.
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Tetrahedron Lett.
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See also ref 16d
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For recent examples of the use of an oxazolidine ring as a glycine surrogate, see: (a) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Tetrahedron Lett. 1999, 40, 5263-5266. (b) Lieberknecht, A.; Griesser, H.; Kramer, B.; Bravo, R. D.; Colinas, P. A.; Grigera, R. J. Tetrahedron 1999, 55, 6475-6482. (c) VanBrunt, M. P.; Standaert, R. F. Org. Lett. 2000, 2, 705-708.
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For recent examples of the use of an oxazolidine ring as a glycine surrogate, see: (a) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Tetrahedron Lett. 1999, 40, 5263-5266. (b) Lieberknecht, A.; Griesser, H.; Kramer, B.; Bravo, R. D.; Colinas, P. A.; Grigera, R. J. Tetrahedron 1999, 55, 6475-6482. (c) VanBrunt, M. P.; Standaert, R. F. Org. Lett. 2000, 2, 705-708.
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For recent examples of the use of an oxazolidine ring as a glycine surrogate, see: (a) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Tetrahedron Lett. 1999, 40, 5263-5266. (b) Lieberknecht, A.; Griesser, H.; Kramer, B.; Bravo, R. D.; Colinas, P. A.; Grigera, R. J. Tetrahedron 1999, 55, 6475-6482. (c) VanBrunt, M. P.; Standaert, R. F. Org. Lett. 2000, 2, 705-708.
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For a preliminary communication, see: Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1998, 39, 6411-6414.
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73
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For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
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74
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For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
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75
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For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
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For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
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See also ref 22 and references therein
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For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
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80
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0343698335
-
-
note
-
Although it has been reported that Michael additions of N-benzylhydroxylamine are favored by the presence of water (see ref 25d), we have not observed such an effect.
-
-
-
-
81
-
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84985553225
-
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In this work we use the syn/anti nomenclature according to Masamune convention. See: Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557-558. Masamune, S.; Kaiho, T.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5521-5523.
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Garvey, D.S.4
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82
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33845555760
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In this work we use the syn/anti nomenclature according to Masamune convention. See: Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557-558. Masamune, S.; Kaiho, T.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5521-5523.
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For a discussion on the selectivity of Micahel addition to γ-alkoxy and γ-amino-α,β-unsaturated esters, see: Hanessian, S.; Sumi, K. Synthesis 1991, 1083-1089.
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0343698343
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note
-
From a preparative standpoint the obtention of mixtures of open-chain and cyclized products was inconsequential since treatment of the reaction mixture with NaOMe in MeOH afforded the desired isoxazolidin-5-ones which are easily purified by flash chromatography (see Scheme 3).
-
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86
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(a) Desai, H. K.; Joshi, B. S.; Panu, A. M.; Pelletier, S. W. J. Chromatogr. 1985, 322, 223-227.
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90
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0342393038
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-
note
-
Purification of cis and trans isomers of 16 and 18 have only analytical purposes. From a synthetic standpoint such a separation is not necessary since those compounds will be used for introducing the base through N-glycosylation.
-
-
-
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91
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0343698341
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note
-
2Si) can be easily prepared (6 steps) from serine in 57.7 and 51.2% overall yields, respectively. See ref 20b.
-
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92
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0342393039
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note
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2AlCl. See ref 19.
-
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93
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(a) Kita, Y.; Itoh, F.; Tamura, O.; Ke, Y. Y.; Tamura, Y. Tetrahedron Lett. 1987, 28, 1431-1434.
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For 1,3-dipolar cycloadditions of nitrones with vinyl acetate, see: (a) DeShong, P.; Dicken, M.; Staib, R. R., Freyer, A. J.; Weinreb, S. M. J. Am. Chem. Soc. 1982, 47, 4397-4403. (b) DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602. (c) Chiacchio, U.; Gumina, G.; Rescifina, A.; Romeo, R.; Uccella, N.; Casuscelli, F.; Piperno, A.; Romeo, G. Tetrahedron 1996, 52, 8889-8898. (d) Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 9322-9327.
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For 1,3-dipolar cycloadditions of nitrones with vinyl acetate, see: (a) DeShong, P.; Dicken, M.; Staib, R. R., Freyer, A. J.; Weinreb, S. M. J. Am. Chem. Soc. 1982, 47, 4397-4403. (b) DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602. (c) Chiacchio, U.; Gumina, G.; Rescifina, A.; Romeo, R.; Uccella, N.; Casuscelli, F.; Piperno, A.; Romeo, G. Tetrahedron 1996, 52, 8889-8898. (d) Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 9322-9327.
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For 1,3-dipolar cycloadditions of nitrones with vinyl acetate, see: (a) DeShong, P.; Dicken, M.; Staib, R. R., Freyer, A. J.; Weinreb, S. M. J. Am. Chem. Soc. 1982, 47, 4397-4403. (b) DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602. (c) Chiacchio, U.; Gumina, G.; Rescifina, A.; Romeo, R.; Uccella, N.; Casuscelli, F.; Piperno, A.; Romeo, G. Tetrahedron 1996, 52, 8889-8898. (d) Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 9322-9327.
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0342827829
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Identical results were obtained when other acids (PPTS, CSA) were used.
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2, employed for the oxidation of amino alcohols is unreliable.
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125
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0342827827
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note
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The overall yields, starting from commercial L-serine, for compound 35a were 11.0% via Michael addition route and 9.5% via nucleophilic addition route. For compound 36a the overall yields, also starting from commercial L-serine, were 7.2% via Michael addition route and 6.2% via nucleophilic addition route.
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126
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0342393031
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note
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The overall yields, starting from commercial L-serine and via 1,3-dipolar cycloaddition route, for cis compounds 45 and 46a were 10.6% and 9.2%, respectively.
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