Total synthesis of (±)-dihydrospiniferin-1 via a polyfluoro alkanosulfonyl fluoride induced tandem carbonium ion rearrangement reaction

Chemical Communications

Volumn 3, Issue 7, 2003, Pages 838-839

  Chen, Ling ^a   Ding, Kai ^a   Tian, Wei Sheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; DIHYDROSPINIFERIN 1; FLUORIDE; GAMMA HYDROXYMETHYLCYCLOHEXENONE; ION; POLYFLUOROALKANOSULFONYL FLUORIDE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; MICHAEL ADDITION; OZONOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0037425309     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b300016h     Document Type: Article

References (22)

1. G. Cimino, S. De Stefano, L. Minale, E. Trivellone, Tetrahedron Lett. 1975, 43, 3727
2. G. Cimino, S. De Stefano, L. Minale, E. Trivellone, Experientia 1978, 34, 1425
3. J. A. Marshall, R. E. Conrow, J. Am. Chem. Soc. 1980, 102, 4274
4. J. A. Marshall, R. E. Conrow, J. Am. Chem. Soc. 1983, 105, 5679
5. E. Vogel, H. D. Roth, Angew. Chem. Int. Ed. Engl. 1964, 3, 228
6. E. Vogel, W. A. Böll, Angew. Chem. Int. Ed. Engl. 1964, 9, 642
7. E. Vogel, W. Pretzer, W. A. Böll, Angew. Chem. Int. Ed. Engl. 1964, 9, 642
8. Z. Zhu, W. S. Tian, Q. J. Liao, Tetrahedron Lett. 1996, 37, 8553
9. Z. Zhu, W. S. Tian, Q. J. Liao, Y. K. Wu, Bioorg. Med. Chem. Lett. 1998, 8, 1949
10. X. S. Feng, W. S. Tian, Q. Y. Chen, Bioorg. Med. Chem. Lett. 1997, 7, 3113
11. X. S. Feng, W. S. Tian, Q. Y. Chen, J. Chem. Soc. Perkin Trans. 1 1998, 6, 1139
12. Z. H. Yan, Ph D dissertation, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 1999
13. W. S. Tian, Z. Lei, L. Chen, Y. Huang, J. Fluorine Chem. 2000, 101, 305
14. Z. Lei, Masters dissertation. Shanghai Institute of Organic Chemistry. Chinese Academy of Sciences. 1997
15. L. Chen, PhD dissertation. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences. 2000
16. S. N. Huckin, L. Weiler, J. Am. Chem. Soc. 1974, 96, 1082
17. M. T. Reetz, I. Chatziiosifidis, K. Schwellnus, Angew. Chem. Int. Ed. Engl. 1981, 20, 687
18. F. W. Sum, L. Weiler, Can. J. Chem. 1979, 57, 1431
19. G. Stork, R. L. Danheiser, J. Org. Chem. 1973, 38, 1775
20. D. Burn, V. Perrow, G. O. Weston, Tetrahedron Lett. 1960, 2, 14
21. D. Burn, J. W. Ducker, B. Ellis, A. K. Hiscock, A. P. Leftwick, C. M. Peach, V. Petrow, D. M. Williamson, J. Chem. Soc. 1963, 4242
22. T. Veysoglu, L. A. Mitscher, J. K. Swayze, Synthesis 1980, 10, 807