A convenient asymmetric access to triquinanic compounds

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2841-2844

  Bintz Giudicelli, C ^a   Weymann, O ^a   Uguen, D ^a   De Cian, A ^b   Fischer, J ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; SESQUITERPENOID; SPIRO COMPOUND;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030914641     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00475-9     Document Type: Article

References (18)

1. Seto, H; Sasaki, T.; Uzawa, J.; Takeuchi, S., Yonehara, H. Tetrahedron Lett. 1978, 19, 4411-4412.
2. a) Sakai, K.; Ohtsuka, T.; Misumi, S.; Shirahama, H.; Matsumoto, T. Chemistry Letters 1981, 355-358;
3. b) Crimmins, M.T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806;
4. c) Ihara, M.; Katogi, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Perkin I 1988, 2963-2970;
5. d) Hudlicky, T.; Sinai-Zingde G.; Natchus, M. G.; Ranu, B. C.; Papadopoulos, P. Tetrahedron 1987, 43, 5685-5721;
6. e) Agnel, G.; Negishi, E.-I. J. Am. Chem. Soc. 1991, 113, 7424-7426;
7. f) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861;
8. g) Wu, J.-Y.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104-110.
9. Bintz, C.; Uguen, D preceding letter in this issue. The results presented herein are taken in parts from the thesis dissertation of C. Bintz (University Louis Pasteur, Strasbourg, 1996).
10. a) Marx, J. N.; Norman, L. R. J. Org. Chem. 1975, 40, 1602-1606;
11. b) Sum, F.-W.; Weiler, L. Can. J. Chem. 1979, 57, 1431-1441. The use of TMSC1, supposed to trap the ethoxide ion which formed theoretically during the substitution process, proved to be essential for obtaining 6b in high yield;
12. c) Kocienski, P.; Todd, M. J. Chem. Soc. Perkin I 1983, 1783-1787.
13. 13C NMR spectra.
14. 3.
15. 2. A CIF has been deposited with the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW (U.K.). They may be obtained on request from the Director by citing the full reference to this communication.
16. Profitt, J. A.; Watt, D. S.; Corey, E. J. J. Org. Chem. 1975, 40, 127-128.
17. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc., 1988, 110, 6917-6918.
18. 1H NMR spectra of that ester displayed basically signals attributable to the ester 4 (see ref. 2c): 0.89 (d, J=6.2 Hz, 3H), 0.93 (s, 3H), 1.04 (s, 3H), 1.15-2.8 (2m, 13H (plus OH), 3.41 (d, J=7.5Hz, 1H), 3.66 (s, 3H).