Electrocyclic ring-opening/π-allyl cation cyclization reaction sequences involving gem-dihalocyclopropanes as substrates: Application to syntheses of (±)-, (+)-, and (-)-γ-lycorane

Journal of Organic Chemistry

Volumn 65, Issue 14, 2000, Pages 4241-4250

  Banwell, Martin G ^a   Harvey, Joanne E ^a   Hockless, David C R ^a   Wu, Angela W ^b  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; DIHALOCYCLOPROPANE; LYCORANE; UNCLASSIFIED DRUG;

ARTICLE; COUPLING FACTOR; CYCLIZATION; DRUG SYNTHESIS; ENZYME SUBSTRATE; PROTEIN MODIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

ALKALOIDS; AMARYLLIDACEAE ALKALOIDS; ANIMALS; CARBOHYDRATE CONFORMATION; CYCLOPROPANES; DISACCHARIDES; ENZYME INHIBITORS; FUCOSYLTRANSFERASES; GLYCOSIDE HYDROLASES; HUMANS; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 0034647544     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991791u     Document Type: Article

References (50)

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21. See: (a) Banwell, M. G.; Berak, M.; Hockless, D. C. R. J. Chem. Soc., Perkin Trans. 1 1996, 2217-2219. (b) Banwell, M. G.; Gable, R. W.; Peters, S. C.; Phyland, J. R. J. Chem. Soc., Chem. Commun. 1995, 1395-1397. (c) Banwell, M. G.; Cowden, C. J.; Gable, R. W. J. Chem. Soc., Perkin Trans. 1 1994, 3515-3518. (d) Banwell, M. G.; Cowden, C. J. Aust. J. Chem. 1994, 47, 2235-2254. (e) Banwell, M. G.; Lambert, J. N.; Gulbis, J. M.; Mackay, M. F. J. Chem. Soc., Chem. Commun. 1990, 1450-1452. (f) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543-4546.
22. See: (a) Banwell, M. G.; Berak, M.; Hockless, D. C. R. J. Chem. Soc., Perkin Trans. 1 1996, 2217-2219. (b) Banwell, M. G.; Gable, R. W.; Peters, S. C.; Phyland, J. R. J. Chem. Soc., Chem. Commun. 1995, 1395-1397. (c) Banwell, M. G.; Cowden, C. J.; Gable, R. W. J. Chem. Soc., Perkin Trans. 1 1994, 3515-3518. (d) Banwell, M. G.; Cowden, C. J. Aust. J. Chem. 1994, 47, 2235-2254. (e) Banwell, M. G.; Lambert, J. N.; Gulbis, J. M.; Mackay, M. F. J. Chem. Soc., Chem. Commun. 1990, 1450-1452. (f) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543-4546.
23. See: (a) Banwell, M. G.; Berak, M.; Hockless, D. C. R. J. Chem. Soc., Perkin Trans. 1 1996, 2217-2219. (b) Banwell, M. G.; Gable, R. W.; Peters, S. C.; Phyland, J. R. J. Chem. Soc., Chem. Commun. 1995, 1395-1397. (c) Banwell, M. G.; Cowden, C. J.; Gable, R. W. J. Chem. Soc., Perkin Trans. 1 1994, 3515-3518. (d) Banwell, M. G.; Cowden, C. J. Aust. J. Chem. 1994, 47, 2235-2254. (e) Banwell, M. G.; Lambert, J. N.; Gulbis, J. M.; Mackay, M. F. J. Chem. Soc., Chem. Commun. 1990, 1450-1452. (f) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543-4546.
24. See: (a) Banwell, M. G.; Berak, M.; Hockless, D. C. R. J. Chem. Soc., Perkin Trans. 1 1996, 2217-2219. (b) Banwell, M. G.; Gable, R. W.; Peters, S. C.; Phyland, J. R. J. Chem. Soc., Chem. Commun. 1995, 1395-1397. (c) Banwell, M. G.; Cowden, C. J.; Gable, R. W. J. Chem. Soc., Perkin Trans. 1 1994, 3515-3518. (d) Banwell, M. G.; Cowden, C. J. Aust. J. Chem. 1994, 47, 2235-2254. (e) Banwell, M. G.; Lambert, J. N.; Gulbis, J. M.; Mackay, M. F. J. Chem. Soc., Chem. Commun. 1990, 1450-1452. (f) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543-4546.
25. See: (a) Banwell, M. G.; Berak, M.; Hockless, D. C. R. J. Chem. Soc., Perkin Trans. 1 1996, 2217-2219. (b) Banwell, M. G.; Gable, R. W.; Peters, S. C.; Phyland, J. R. J. Chem. Soc., Chem. Commun. 1995, 1395-1397. (c) Banwell, M. G.; Cowden, C. J.; Gable, R. W. J. Chem. Soc., Perkin Trans. 1 1994, 3515-3518. (d) Banwell, M. G.; Cowden, C. J. Aust. J. Chem. 1994, 47, 2235-2254. (e) Banwell, M. G.; Lambert, J. N.; Gulbis, J. M.; Mackay, M. F. J. Chem. Soc., Chem. Commun. 1990, 1450-1452. (f) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543-4546.
26. For some earlier examples of cationic cyclizations initiated by electrocyclic cleavage of gem-dibromocyclopropanes see: (a) Gassman, P. G.; Tan, L.; Hoye, T. R. Tetrahedron Lett. 1996, 37, 439-442. (b) Hemmingsen, T. H.; Svendsen, J. S.; Sydnes, L. K. Acta Chem. Scand. 1988, B42, 651-661. (c) Brocksom, T. J.; Canevarolo, E. T.; Lopes, F. T. An. Acad. Bras. Cienc. 1985, 57, 165-168; Chem. Abs. 1986, 105, 191422. (d) Danheiser, R. L.; Morin, J. M.; Salaski, E. J. J. Am. Chem. Soc. 1985, 107, 8066-8073. (e) Danheiser, R. L.; Morin, J. M.; Yu, M.; Basak, A. Tetrahedron Lett. 1981, 22, 4205-4208.
27. For some earlier examples of cationic cyclizations initiated by electrocyclic cleavage of gem-dibromocyclopropanes see: (a) Gassman, P. G.; Tan, L.; Hoye, T. R. Tetrahedron Lett. 1996, 37, 439-442. (b) Hemmingsen, T. H.; Svendsen, J. S.; Sydnes, L. K. Acta Chem. Scand. 1988, B42, 651-661. (c) Brocksom, T. J.; Canevarolo, E. T.; Lopes, F. T. An. Acad. Bras. Cienc. 1985, 57, 165-168; Chem. Abs. 1986, 105, 191422. (d) Danheiser, R. L.; Morin, J. M.; Salaski, E. J. J. Am. Chem. Soc. 1985, 107, 8066-8073. (e) Danheiser, R. L.; Morin, J. M.; Yu, M.; Basak, A. Tetrahedron Lett. 1981, 22, 4205-4208.
28. For some earlier examples of cationic cyclizations initiated by electrocyclic cleavage of gem-dibromocyclopropanes see: (a) Gassman, P. G.; Tan, L.; Hoye, T. R. Tetrahedron Lett. 1996, 37, 439-442. (b) Hemmingsen, T. H.; Svendsen, J. S.; Sydnes, L. K. Acta Chem. Scand. 1988, B42, 651-661. (c) Brocksom, T. J.; Canevarolo, E. T.; Lopes, F. T. An. Acad. Bras. Cienc. 1985, 57, 165-168; Chem. Abs. 1986, 105, 191422. (d) Danheiser, R. L.; Morin, J. M.; Salaski, E. J. J. Am. Chem. Soc. 1985, 107, 8066-8073. (e) Danheiser, R. L.; Morin, J. M.; Yu, M.; Basak, A. Tetrahedron Lett. 1981, 22, 4205-4208.
29. For some earlier examples of cationic cyclizations initiated by electrocyclic cleavage of gem-dibromocyclopropanes see: (a) Gassman, P. G.; Tan, L.; Hoye, T. R. Tetrahedron Lett. 1996, 37, 439-442. (b) Hemmingsen, T. H.; Svendsen, J. S.; Sydnes, L. K. Acta Chem. Scand. 1988, B42, 651-661. (c) Brocksom, T. J.; Canevarolo, E. T.; Lopes, F. T. An. Acad. Bras. Cienc. 1985, 57, 165-168; Chem. Abs. 1986, 105, 191422. (d) Danheiser, R. L.; Morin, J. M.; Salaski, E. J. J. Am. Chem. Soc. 1985, 107, 8066-8073. (e) Danheiser, R. L.; Morin, J. M.; Yu, M.; Basak, A. Tetrahedron Lett. 1981, 22, 4205-4208.
30. For some earlier examples of cationic cyclizations initiated by electrocyclic cleavage of gem-dibromocyclopropanes see: (a) Gassman, P. G.; Tan, L.; Hoye, T. R. Tetrahedron Lett. 1996, 37, 439-442. (b) Hemmingsen, T. H.; Svendsen, J. S.; Sydnes, L. K. Acta Chem. Scand. 1988, B42, 651-661. (c) Brocksom, T. J.; Canevarolo, E. T.; Lopes, F. T. An. Acad. Bras. Cienc. 1985, 57, 165-168; Chem. Abs. 1986, 105, 191422. (d) Danheiser, R. L.; Morin, J. M.; Salaski, E. J. J. Am. Chem. Soc. 1985, 107, 8066-8073. (e) Danheiser, R. L.; Morin, J. M.; Yu, M.; Basak, A. Tetrahedron Lett. 1981, 22, 4205-4208.
31. For some earlier examples of cationic cyclizations initiated by electrocyclic cleavage of gem-dibromocyclopropanes see: (a) Gassman, P. G.; Tan, L.; Hoye, T. R. Tetrahedron Lett. 1996, 37, 439-442. (b) Hemmingsen, T. H.; Svendsen, J. S.; Sydnes, L. K. Acta Chem. Scand. 1988, B42, 651-661. (c) Brocksom, T. J.; Canevarolo, E. T.; Lopes, F. T. An. Acad. Bras. Cienc. 1985, 57, 165-168; Chem. Abs. 1986, 105, 191422. (d) Danheiser, R. L.; Morin, J. M.; Salaski, E. J. J. Am. Chem. Soc. 1985, 107, 8066-8073. (e) Danheiser, R. L.; Morin, J. M.; Yu, M.; Basak, A. Tetrahedron Lett. 1981, 22, 4205-4208.
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