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Volumn 11, Issue 13, 2009, Pages 2896-2899

Efficient asymmetrie synthesis of chiral hydroxy-y-butyrolactones

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; GAMMA BUTYROLACTONE; OXAZOLIDINONE DERIVATIVE;

EID: 67649491241     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9008365     Document Type: Article
Times cited : (16)

References (48)
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    • (a) Anticancer: Popsavin, V.; Benedekovic, G.; Sreco, B.; Popsavin, M.; Francuz, J.; Kojic, V.; Bogdanovic, G. Org. Lett. 2007, 9, 4235.
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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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    • 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.
    • 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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    • 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.
    • 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 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,
    • 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,
  • 26
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    • For previous reports of γ,δ-epoxides of tertiary amides cyclizing to afford y-lactones, see: a
    • 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.
    • (1984) J. Chem. Soc., Chem. Commun , pp. 1487
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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
    • 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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    • 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.
    • 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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    • Reference 4b
    • (c) Reference 4b.
  • 39
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    • 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
    • 67649540099 scopus 로고    scopus 로고
    • 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
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    • For other polymer-supported oxazolidin-2-one aldol reactions, see: a
    • For other polymer-supported oxazolidin-2-one aldol reactions, see: (a) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777.
    • (1997) Tetrahedron Lett , vol.38 , pp. 8777
    • Purandare, A.V.1    Natarajan, S.2
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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.
    • (1992) J. Org. Chem , vol.57 , pp. 6088
    • Moon, H.S.1    Schore, N.E.2    Kurth, M.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.