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Volumn 68, Issue 5, 2003, Pages 1919-1928

Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS; LACTAM;

EID: 0037424287     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0266083     Document Type: Article
Times cited : (161)

References (108)
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    • See also ref 2c
    • (c) See also ref 2c.
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    • (a) Lactam 1 (or its enantiomer) has also been prepared by alternative procedures: Royer, J.; Husson, H.-P. Heterocycles 1993, 36, 1493-1496.
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    • (b) For a disscusion on the stereoselectivity of allyltrimethylsilane α-amidoalkylations to related -phenylglycinol- or-1-phenylethylamine-derived δ- and γ-lactams, see: Polniaszek, R. P.; Belmont, S. E.; Alvarez, R. J. Org. Chem. 1990, 55, 215-223.
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    • Interestingly, the reaction of 1 with PrMgBr takes place with opposite diastereoselectivity to give piperidone 5b as the major product: see ref 10c
    • (e) Interestingly, the reaction of 1 with PrMgBr takes place with opposite diastereoselectivity to give piperidone 5b as the major product: see ref 10c.
  • 47
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    • For a preliminary account of this part of the work, see ref 9a
    • For a preliminary account of this part of the work, see ref 9a.
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    • (b) For the use of organocopper derivatives in intermolecular α-amidoalkylation reactions, see: Ludwig, C.; Wistrand, L.-G. Acta Chem. Scand. 1994, 48, 367-371.
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    • In the major isomers a the methine benzylic proton appears more shielded, and both the benzylic and C-6 carbons more deshielded, than in the minor isomers b
    • (a) In the major isomers a the methine benzylic proton appears more shielded, and both the benzylic and C-6 carbons more deshielded, than in the minor isomers b
  • 60
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    • (a) For related approaches, involving the reductive ring-opening of phenylglycinol-derived 8a-substituted bicyclic δ-lactams, see: Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084-7085.
    • (1995) J. Org. Chem. , vol.60 , pp. 7084-7085
    • Munchhof, M.J.1    Meyers, A.I.2
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    • (b) For related highly stereoselective approaches to α- and β-C-glycopyranosides, see: Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
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    • 2) is indicative of a 2,6-cis relationship, whereas the trans isomers show a slightly negative value: Yue, C.; Nicolay, J.-F.; Royer, J.; Husson, H.-P. Tetrahedron 1994, 50, 3139-3148.
    • (1994) Tetrahedron , vol.50 , pp. 3139-3148
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    • To avoid confusion with other reports, it must be noted that, according to the IUPAC recommendations, we assign the lower locant (i.e., 2) to the chain that should be cited first in the name (i.e., methyl)
    • (a) To avoid confusion with other reports, it must be noted that, according to the IUPAC recommendations, we assign the lower locant (i.e., 2) to the chain that should be cited first in the name (i.e., methyl).
  • 75
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    • 23a,b and that, therefore, dihydropinidine is levorotatory. There is also a confusion in the literature in this respect
    • 23a,b and that, therefore, dihydropinidine is levorotatory. There is also a confusion in the literature in this respect.
  • 80
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    • (a) For recent enantioselective syntheses of indolizidine 167B, see: Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467.
    • (2000) Org. Lett. , vol.2 , pp. 465-467
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    • Attempts to generate a Grignard reagent from several 1-halo-3-heptanone acetals were unsuccessful
    • Attempts to generate a Grignard reagent from several 1-halo-3-heptanone acetals were unsuccessful.
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    • 3MgCl to give, after hydride reduction, trans-2,6-dimethylpiperidine 26 (R = H): see ref 16b
    • 3MgCl to give, after hydride reduction, trans-2,6-dimethylpiperidine 26 (R = H): see ref 16b.
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    • (a) Isolation: Kuzovkov, A. D.; Menshikov, G. P. Zh. Obshch. Khim. 1950, 20, 1524-1527; Chem. Abstr. 1951, 45, 2485g
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    • It must be noted that lupetidine base is levorotatory
    • (c) It must be noted that lupetidine base is levorotatory.
  • 95
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    • See also ref 16b
    • (d) For previous enantioselective syntheses, see: Najdi, S.; Kurth, M. J. Tetrahedron Lett. 1990, 31, 3279-3282. See also ref 16b.
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    • See also ref 7e
    • (e) For the synthesis of ent-lupetidine (2S,6S), see: Adamo, M. F. A.; Aggarwal, V. K.; Sage, M. A. Synth. Commun. 1999, 29, 1747-1756. See also ref 7e.
    • (1999) Synth. Commun. , vol.29 , pp. 1747-1756
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  • 101
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    • For previous enantioselective syntheses, see ref 14a and references cited therein
    • (a) For previous enantioselective syntheses, see ref 14a and references cited therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.