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2
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0032959978
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Antibiotic: Matsumoto, N.; Tsuchida, T.; Maruyama, M.; Kinoshita, N.; Homma, Y.; Iinuma, H.; Sawa, T.; Hamada, M.; Takeuchi, T.; Heida, N.; Yoshioka, T. J. Antibiot. 1999, 52, 269.
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(b) Antibiotic: Matsumoto, N.; Tsuchida, T.; Maruyama, M.; Kinoshita, N.; Homma, Y.; Iinuma, H.; Sawa, T.; Hamada, M.; Takeuchi, T.; Heida, N.; Yoshioka, T. J. Antibiot. 1999, 52, 269.
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3
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33750435912
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Antifungal: Larrosa, I.; Da Silva, M. L; Gomez, P. M.; Hannen, P.; Ko, E.; Lenger, S. R.; Linke, S. R.; White, A. J. P.; Wilton, D.; Barrett, A. G. M. J. Am. Chem. Soc. 2006, 128, 14042.
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(c) Antifungal: Larrosa, I.; Da Silva, M. L; Gomez, P. M.; Hannen, P.; Ko, E.; Lenger, S. R.; Linke, S. R.; White, A. J. P.; Wilton, D.; Barrett, A. G. M. J. Am. Chem. Soc. 2006, 128, 14042.
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0034730017
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Aldol substrates 2a-i prepared via reaction of the boron or magnesium enolate of an N-propionyloxazolidin-2-one with the corresponding α,β-unsaturated aldehyde: (a) Caddick, S.; Parr, N. J.; Pritchard, M. C. Tetrahedron Lett. 2000, 41, 5963.
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Aldol substrates 2a-i prepared via reaction of the boron or magnesium enolate of an N-propionyloxazolidin-2-one with the corresponding α,β-unsaturated aldehyde: (a) Caddick, S.; Parr, N. J.; Pritchard, M. C. Tetrahedron Lett. 2000, 41, 5963.
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24
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0028260070
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For a report of a 50:50 mixture of stable diastereoisomeric epoxides prepared by epoxidation of a γ,δ-unsaturated N-acyloxazoLidin-2-one with m-chloroperoxybenzoic acid, see: Trova, M. P.; Wissner, A.; Casscles, W. T., Jr.; Hsu, G. C. Bioorg. Med. Chem. Lett. 1994, 4, 903.
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For a report of a 50:50 mixture of stable diastereoisomeric epoxides prepared by epoxidation of a γ,δ-unsaturated N-acyloxazoLidin-2-one with m-chloroperoxybenzoic acid, see: Trova, M. P.; Wissner, A.; Casscles, W. T., Jr.; Hsu, G. C. Bioorg. Med. Chem. Lett. 1994, 4, 903.
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0012460303
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For aldol reaction of the boron enolate of an Evans' N-acyloxazolidin2- one with, an α,β-epoxy aldehyde that gave a stable γ,δ-epoxy aldol product, see: Taylor, R. E.; Hearn, B. R.; Ciavam, J. P. Org. Lett. 2002, 4, 2953,
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For aldol reaction of the boron enolate of an Evans' N-acyloxazolidin2- one with, an α,β-epoxy aldehyde that gave a stable γ,δ-epoxy aldol product, see: Taylor, R. E.; Hearn, B. R.; Ciavam, J. P. Org. Lett. 2002, 4, 2953,
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26
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37049110839
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For previous reports of γ,δ-epoxides of tertiary amides cyclizing to afford y-lactones, see: a
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For previous reports of γ,δ-epoxides of tertiary amides cyclizing to afford y-lactones, see: (a) Cairns, P. M.; Howes, C.; Jenkins, P. R.; Russell, D. R.; Sherry, L. J. Chem. Soc., Chem. Commun. 1984, 1487.
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28
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0031012715
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An alternative mechanism involving intramolecular 6-endo-tet ringopening of erythro-epoxide 4a with retention of configuration at C4 was discounted because rearrangement of the resultant ¿-lactone would have afforded a diastereoisomeric (2S,3S,4R)-y-lactone; see: (a) Nacro, K, Baltas, M, Escudier, J. M, Gorrichon, L. Tetrahedron 1997, 53, 659
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An alternative mechanism involving intramolecular 6-endo-tet ringopening of erythro-epoxide 4a with retention of configuration at C4 was discounted because rearrangement of the resultant ¿-lactone would have afforded a diastereoisomeric (2S,3S,4R)-y-lactone; see: (a) Nacro, K.; Baltas, M.; Escudier, J. M.; Gorrichon, L. Tetrahedron 1997, 53, 659.
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(b) Nacro, K.; Baltas, M.; Zedde, C.; Gorrichon, L.; Jaud, J. Tetrahedron 1999, 55, 5129.
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See: (a) Yokomatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728.
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35
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67649543401
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ent-Lacton.es 8b and 8f have been prepared previously via directed epoxidation of β-vinyl-syn-aldol esters; see: (a) McCarthy, P. A. Tetrahedron Lett. 1982, 23, 4.199.
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ent-Lacton.es 8b and 8f have been prepared previously via directed epoxidation of β-vinyl-syn-aldol esters; see: (a) McCarthy, P. A. Tetrahedron Lett. 1982, 23, 4.199.
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36
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0023891875
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(b) Nakata, T.; Fukui, M.; Oishi, T. Tetrahedron Lett. 1988, 29, 2219.
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67649570766
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Reference 4b
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(c) Reference 4b.
-
-
-
-
39
-
-
67649565083
-
-
Repeated attempts to epoxidize a monosubstituted syn-aldol product derived from acrolein under these conditions were unsuccessful, affording only recovered starting material
-
Repeated attempts to epoxidize a monosubstituted syn-aldol product derived from acrolein under these conditions were unsuccessful, affording only recovered starting material.
-
-
-
-
40
-
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67649540099
-
-
1H NMR experiment revealed strong (S) interactions consistent with the proposed (S,S,S) configuration of γ-lactone 8h, which implies that all of the epoxides 4a-i are ring-opening via the intramolecular 5-exo-tet pathway shown in. Scheme 2. equation prensented
-
1H NMR experiment revealed strong (S) interactions consistent with the proposed (S,S,S) configuration of γ-lactone 8h, which implies that all of the epoxides 4a-i are ring-opening via the intramolecular 5-exo-tet pathway shown in. Scheme 2. equation prensented
-
-
-
-
41
-
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0041830946
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See: a
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See: (a) Green, R.; Taylor, P. J. M.; Bull, S. D.; James, T. D.; Mahon, M. F.; Merritt, A. T. Tetrahedron: Asymmetry 2003, 14, 2619.
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0030733231
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For other polymer-supported oxazolidin-2-one aldol reactions, see: a
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For other polymer-supported oxazolidin-2-one aldol reactions, see: (a) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777.
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0026679220
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For asymmetric syntheses of chiral lactones using other polymersupported chiral auxiliaries, see: a
-
For asymmetric syntheses of chiral lactones using other polymersupported chiral auxiliaries, see: (a) Moon, H. S.; Schore, N. E.; Kurth., M. J. J. Org. Chem. 1992, 57, 6088.
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