Total synthesis of(±)=dictamnol by a free radical fragmentation/elimination sequence. Confirmation of its revised structure

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6371-6374

  Lange, Gordon L ^a   Merica, Alexandru ^a   Chimanikire, Melerin ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DICTAMNOL; SESQUITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030765702     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01466-4     Document Type: Article

References (15)

1. Takeuchi, N.; Fujita, T.; Goto, K.; Morisaki, N.; Osone, N.; Tobinaga, S. Chem. Pharm. Bull. 1993, 41, 923.
2. Koike, T.; Yamazaki, K.; Fukumoto, N.; Yashiro, K.; Takeuchi, N.; Tobinaga, S. Chem. Pharm. Bull. 1996, 44, 646.
3. Piet, D.P.; Orru, R.V.A.; Jenniskens, L.H.D.; van de Haar, C.; van Beek, T.A.; Franssen, M.C.R.; Wijnberg, J.B.P.A.; de Groot, A. Chem. Pharm. Bull. 1996, 44, 1400.
4. Lange, G.L.; Gottardo, C. Tetrahedron Lett. 1990, 31, 5985.
5. Lange, G.L.; Gottardo, C. J. Org. Chem. 1995, 60, 2183.
6. Free radical fragmentation of other cyclobutyl carbinyl systems has been reported: (a) Ziegler, F. E.; Zheng, Z.-L. J. Org. Chem. 1990, 55, 1416. (b) Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519.
7. Free radical fragmentation of other cyclobutyl carbinyl systems has been reported: (a) Ziegler, F. E.; Zheng, Z.-L. J. Org. Chem. 1990, 55, 1416. (b) Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519.
8. Free radical fragmentation of other cyclobutyl carbinyl systems has been reported: (a) Ziegler, F. E.; Zheng, Z.-L. J. Org. Chem. 1990, 55, 1416. (b) Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519.
9. Lange, G.L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513.
10. Lange, G.L.; Gottardo, C. Synth. Commun. 1990, 20, 1473.
11. Free radicals have been suggested as intermediates in the formation of Grignard reagents: (a) Ashby, E. C.; Oswald, J. J. Org. Chem. 1988, 53, 6068. (b) Walling, C. Acc. Chem. Res. 1991, 24, 255.
12. Free radicals have been suggested as intermediates in the formation of Grignard reagents: (a) Ashby, E. C.; Oswald, J. J. Org. Chem. 1988, 53, 6068. (b) Walling, C. Acc. Chem. Res. 1991, 24, 255.
13. 7 double bond migration into conjugation.
14. 3
15. 2 required 13 steps.