Dioxirane epoxidation of 10-membered-ring stilbene lactams as synthetic precursors to protoberberines

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 877-883

  Rodríguez, Gema ^a   Castedo, Luis ^a   Domínguez, Domingo ^a   Saá, Carlos ^a   Adam, Waldemar ^b   Saha Möller, Chantu R ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM DERIVATIVE; PROTOBERBERINE DERIVATIVE; STILBENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; EPOXIDATION; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0040637874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981829n     Document Type: Article

References (30)

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8. For a review of the chemistry of dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822. (d) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599. (e) Adam, W.; Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Gasparrini, F.; Kluge, R.; Paredes, R.; Schulz, M.; Smerz, A. K.; Veloza, L. A., Weinkötz, S.; Winde, R. Chem. Eur. J. 1997, 3, 105-109.
9. For a review of the chemistry of dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822. (d) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599. (e) Adam, W.; Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Gasparrini, F.; Kluge, R.; Paredes, R.; Schulz, M.; Smerz, A. K.; Veloza, L. A., Weinkötz, S.; Winde, R. Chem. Eur. J. 1997, 3, 105-109.
10. For a review of the chemistry of dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822. (d) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599. (e) Adam, W.; Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Gasparrini, F.; Kluge, R.; Paredes, R.; Schulz, M.; Smerz, A. K.; Veloza, L. A., Weinkötz, S.; Winde, R. Chem. Eur. J. 1997, 3, 105-109.
11. For a review of the chemistry of dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822. (d) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599. (e) Adam, W.; Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Gasparrini, F.; Kluge, R.; Paredes, R.; Schulz, M.; Smerz, A. K.; Veloza, L. A., Weinkötz, S.; Winde, R. Chem. Eur. J. 1997, 3, 105-109.
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14. NOE studies and molecular modeling did not allow to assign unequivocally the geometry of the isolated stereoisomer.
15. Use of less DMD (1.1-4 equiv) led to incomplete consumption of the starting material (18% to 77% conversion) in 24 h.
16. Regardless of the amount of DMD used, both 2a and 9 appeared in the early stages of the reaction, as was shown by TLC monitoring.
17. 75% of starting epoxysilane 2a was recovered unchanged.
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27. Compound 13 persists in acetone solution; however, in the presence of DMD, a slow dehydration takes place to afford 3a. (19) Geometry optimization was carried out by PM3 semiempirical calculations by using MacSpartan Plus 1.1.6, Wave Function, Irvine, CA, 1996.
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