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Volumn 110, Issue 26, 1988, Pages 8696-8698

Stereoselective Synthesis of (±)-Indolizidines 167B, 205A, and 207A. Enantioselective Synthesis of (-)-Indolizidine 209B

Author keywords

[No Author keywords available]

Indexed keywords

5 PROPYLINDOLIZIDINE; 8 METHYL 5 (4 PENTENYL)INDOLIZIDINE; 8 METHYL 5 (4 PENTYNYL)INDOLIZIDINE; UNCLASSIFIED DRUG;

EID: 0024204460     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00234a021     Document Type: Article
Times cited : (69)

References (19)
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    • Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W.; Ed.; Wiley: New York, 1986; Vol. 4, Chapter 1, pp 1–274. (b) Daly, J. W.; Myers, C. W.; Whittaker, N. Toxicon 1987, 25, 1023–1095. (c) Tokuyama, T.; Nishimori, N.; Shimada, A.; Edwards, M. W.; Daly, J. W. Tetrahedron 1987, 43, 643–652.
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    • Indolizidine 223AB has been synthesized by more than one strategy, and its structure and absolute stereochemistry have been defined as (3R, 5R, 8aR)-3-butyl-5-propylindolizidine
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    • Indolizidine 223AB has been synthesized by more than one strategy, and its structure and absolute stereochemistry have been defined as (3R,5R,8aR)-3-butyl-5-propylindolizidine: (a) MacDonald, T. L. J. Org. Chem. 1980, 45, 193–194. (b) Hart, D. J.; Tsai, Y.-M. J. Org. Chem. 1982, 47, 4403–4409. (c) Broka, C. A.; Eng, K. K. J. Org. Chem. 1986, 51, 5043–5045. (d) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Am. Chem. Soc. 1985, 107, 5534–5535. (e) Royer, J.; Husson, H.-P. Tetrahedron Lett. 1985, 26, 1515–1518.
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    • Padwa, A., Ed.; Wiley-Interscience: New York Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1–173. (b) For related intramolecular nitrone cycloadditions, see: Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.; Petrzilka, M. Tetrahedron Lett. 1979, 20, 4391–4394. Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.; Petrzilka, M. Tetrahedron 1985, 41, 3497–3509. Holmes, A. B.; Swithenbank, C.; Williams, S. F. J. Chem. Soc., Chem. Commun. 1986, 265–266
    • Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 2, Chapter 12, pp 277–406. Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1–173. (b) For related intramolecular nitrone cycloadditions, see: Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.; Petrzilka, M. Tetrahedron Lett. 1979, 20, 4391–4394. Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.; Petrzilka, M. Tetrahedron 1985, 41, 3497–3509. Holmes, A. B.; Swithenbank, C.; Williams, S. F. J. Chem. Soc., Chem. Commun. 1986, 265–266.
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    • Comparison of the synthetic material with an authentic sample (GC/MS) by Dr. T. Spande (NIH) showed the two to be identical and hence confirmed the assigned structure. (b) The synthetic sample was found to be identical with the natural material by NMR, IR, MS, and GC (Dr. J. W. Daly, personal communication)
    • Comparison of the synthetic material with an authentic sample (GC/MS) by Dr. T. Spande (NIH) showed the two to be identical and hence confirmed the assigned structure. (b) The synthetic sample was found to be identical with the natural material by NMR, IR, MS, and GC (Dr. J. W. Daly, personal communication).
  • 15
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    • A few α-chiral nitrones have been prepared and used in intramolecular cycloaddition reactions
    • These were, however, C-alkenylnitrones and hence did not require the formation of α-chiral N-alkenylhydroxylamines. See Baggiolini, E. G.; Lee, H. L.; Pizzolato, G.; Uskoković, M. R. J. Am. Chem. Soc. 1982, 104, 6460–6462
    • A few α-chiral nitrones have been prepared and used in intramolecular cycloaddition reactions. These were, however, C-alkenylnitrones and hence did not require the formation of α-chiral N-alkenylhydroxylamines. See: Wovkulich, P. M.; Uskoković, M. R. J. Am. Chem. Soc. 1981, 103, 3958–3959. Baggiolini, E. G.; Lee, H. L.; Pizzolato, G.; Uskoković, M. R. J. Am. Chem. Soc. 1982, 104, 6460–6462.
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    • Cuprate displacement of tosvlate
    • The aldehyde 32 was found to be in the form of the corresponding hemi-aminal. (c) Wittig olefination: Greenwald, R.; Chaykovsky, M.; Corey, E. J. J. Org. Chem. 1963, 28, 1128–1129.
    • Cuprate displacement of tosvlate: Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7777–7782, 7783–7788. (b) The aldehyde 32 was found to be in the form of the corresponding hemi-aminal. (c) Wittig olefination: Greenwald, R.; Chaykovsky, M.; Corey, E. J. J. Org. Chem. 1963, 28, 1128–1129.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.