Asymmetric synthesis of palitantin from the (5R)-tert-butyldimenthylsiloxy-2-cyclohexenone

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7493-7496

  Hareau, Georges ^a   Koiwa, Masakazu ^a   Hanazawa, Takeshi ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis; Copper; Copper compounds; Cyclohexenones; Hydroxylation

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; COPPER; COPPER DERIVATIVE; PALITANTIN; UNCLASSIFIED DRUG;

ARTICLE; HYDROXYLATION; PARTIAL DRUG SYNTHESIS; STEREOCHEMISTRY;

FELIS CATUS;

EID: 0033569971     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01549-X     Document Type: Article

References (17)

1. (a) Hikichi, S.; Hareau, G.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Hareau, G.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099, and Angew. Chem. 1998, 110, 2221. (c) Hareau, G.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640.
2. (a) Hikichi, S.; Hareau, G.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Hareau, G.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099, and Angew. Chem. 1998, 110, 2221. (c) Hareau, G.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640.
3. (a) Hikichi, S.; Hareau, G.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Hareau, G.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099, and Angew. Chem. 1998, 110, 2221. (c) Hareau, G.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640.
4. (a) Hikichi, S.; Hareau, G.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Hareau, G.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099, and Angew. Chem. 1998, 110, 2221. (c) Hareau, G.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640.
5. Birkinshaw, J. H.; Raistvick, H. Biochem. J. 1936, 30, 801. Birkinshaw, J. H. Biochem. J. 1952, 51, 271. Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662.
6. Birkinshaw, J. H.; Raistvick, H. Biochem. J. 1936, 30, 801. Birkinshaw, J. H. Biochem. J. 1952, 51, 271. Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662.
7. Birkinshaw, J. H.; Raistvick, H. Biochem. J. 1936, 30, 801. Birkinshaw, J. H. Biochem. J. 1952, 51, 271. Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662.
8. Curtis, P. J.; Hemming, H. G.; Smith, W. K. Nature 1951, 167, 557.
9. Ichihara, A.; Ubukata, M.; Sakamura, S. Tetrahedron 1980, 36, 1547, and Tetrahedron Lett. 1977, 3473.
10. Ichihara, A.; Ubukata, M.; Sakamura, S. Tetrahedron 1980, 36, 1547, and Tetrahedron Lett. 1977, 3473.
11. Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
12. Deruyttere, X.; Dumortier, L.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 51.
13. 4-dihydroxylation, see: Schröder, M. Chem. Rev. 1980, 80, 187.
14. Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495.
15. The commercial THF solution (5% water) was first evaporated, then freeze-dried for 12 h.
16. Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440.
17. 13C NMR: δ 206.8, 134.1, 133.9, 130.0, 129.7, 79.0, 74.5, 45.8, 38.4, 35.6, 34.6, 22.3, 13.6, 0.2, 0.1. Birkinshaw, J. H. Biochem. J. 1952, 51, 271. Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662. Birkinshaw, J. H. Biochem. J. 1952, 51, 271. Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662. Birkinshaw, J. H. Biochem. J. 1952, 51, 271. Bowden, K.; Lythgoe, B.; Marsden, D. J. S. J. Chem. Soc. 1959, 1662.