General strategy toward the tetrahydronaphthalene skeleton. An expedient total synthesis of sertraline

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5246-5247

  Lautens, Mark ^a   Rovis, Tomislav ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

SERTRALINE; TETRALIN DERIVATIVE;

ARTICLE; CATALYSIS; DEPRESSION; DRUG SYNTHESIS; ORGANIC CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030857960     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971115x     Document Type: Article

References (22)

1. (a) Welch, W. M.; Kraska, A. R.; Sarges, R.; Koe, B. K. J. Med. Chem. 1984, 27, 1508.
2. (b) Williams, M.; Quallich, G. Chem. Ind. (London) 1990, 10, 315.
3. (c) Quallich, G. J.; Woodall, T. M. Tetrahedron 1992, 48, 10239.
4. (d) Corey, E. J.; Gant, T. G. Tetrahedron Lett. 1994, 35, 5373.
5. (e) Johnson, B. M.; Chang, P.-T. L. Anal. Profiles Drug Subst. 1996, 24, 443.
6. Kamal, A.; Gayatri, N. L. Tetrahedron Lett. 1996, 37, 3359 and references therein
7. Fieser, L. F.; Haddadin, M. J. Can. J. Chem. 1965, 43, 1599.
8. Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. For an early attempt at asymmetric hydroalumination see: Giacomelli, G.; Bertero, L.; Lardicci, L. Tetrahedron Lett. 1981, 22, 883.
9. Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. For an early attempt at asymmetric hydroalumination see: Giacomelli, G.; Bertero, L.; Lardicci, L. Tetrahedron Lett. 1981, 22, 883.
10. For a racemic route to 6 from 5, see; Brown, H. C.; Vara Prasad, J. V. N. J. Org. Chem. 1985, 50, 3002. Alcohol 6 has been isolated in high ee from the microbial oxidation of dihydronaphthalene (62% yield). (a) Boyd, D. R.; McMordie, R. A. S.; Sharma, N. D.; Dalton, H.; Williams, P.; Jenkins, R. O. J. Chem. Soc., Chem. Commun 1989, 339. (b) Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H.; J. Chem. Soc., Perkin Trans. 1 1996, 67.
11. For a racemic route to 6 from 5, see; Brown, H. C.; Vara Prasad, J. V. N. J. Org. Chem. 1985, 50, 3002. Alcohol 6 has been isolated in high ee from the microbial oxidation of dihydronaphthalene (62% yield). (a) Boyd, D. R.; McMordie, R. A. S.; Sharma, N. D.; Dalton, H.; Williams, P.; Jenkins, R. O. J. Chem. Soc., Chem. Commun. 1989, 339. (b) Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H.; J. Chem. Soc., Perkin Trans. 1 1996, 67.
12. For a racemic route to 6 from 5, see; Brown, H. C.; Vara Prasad, J. V. N. J. Org. Chem. 1985, 50, 3002. Alcohol 6 has been isolated in high ee from the microbial oxidation of dihydronaphthalene (62% yield). (a) Boyd, D. R.; McMordie, R. A. S.; Sharma, N. D.; Dalton, H.; Williams, P.; Jenkins, R. O. J. Chem. Soc., Chem. Commun. 1989, 339. (b) Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McMordie, R. A. S.; Sheldrake, G. N.; Williams, P.; Dalton, H.; J. Chem. Soc., Perkin Trans. 1 1996, 67.
13. For a study of the relative tendencies of some aromatic hydrates to aromatize, see: Rao, S. N.; More O'Ferrall, R. A.; Kelly, S. C.; Boyd, D. R.; Agarwal, R. J. Am. Chem. Soc. 1993, 115, 5458.
14. Willems, A. G. M.; Pandit, U. K.; Huisman, H. O. Recl. Trav. Chim. Pays-Bas 1965, 84, 389.
15. Farina, V. Pure Appl. Chem. 1996, 68, 73 and references therein.
16. For a review on the directed homogeneous hydrogenation, see: Brown, J. M. Angew. Chem., Int. Ed. Engl. 1987, 26, 190. For a recent review encompassing directed hydrogenations, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. Following completion of our work, a report appeared in the literature describing the use of the cationic rhodium complex in the directed hydrogenation of a dihydronaphthalenol: Kuroda, T.; Takahashi, M.; Kondo, K.; Iwasaki, T, J. Org. Chem. 1996, 61, 9560.
17. For a review on the directed homogeneous hydrogenation, see: Brown, J. M. Angew. Chem., Int. Ed. Engl. 1987, 26, 190. For a recent review encompassing directed hydrogenations, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. Following completion of our work, a report appeared in the literature describing the use of the cationic rhodium complex in the directed hydrogenation of a dihydronaphthalenol: Kuroda, T.; Takahashi, M.; Kondo, K.; Iwasaki, T, J. Org. Chem. 1996, 61, 9560.
18. For a review on the directed homogeneous hydrogenation, see: Brown, J. M. Angew. Chem., Int. Ed. Engl. 1987, 26, 190. For a recent review encompassing directed hydrogenations, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. Following completion of our work, a report appeared in the literature describing the use of the cationic rhodium complex in the directed hydrogenation of a dihydronaphthalenol: Kuroda, T.; Takahashi, M.; Kondo, K.; Iwasaki, T, J. Org. Chem. 1996, 61, 9560.
19. For a seminal reference, see: Stork, G.; Kahne, D. E. J. Am. Chem. Soc. 1983, 105, 1072. For a synthesis of Crabtree's catalyst, see: Crabtree, R. H.; Morehouse, S. M. Inorganic Syntheses; Shreeve, J. M., Ed.; Wiley: New York, 1986; Vol. 24, p 173.
20. For a seminal reference, see: Stork, G.; Kahne, D. E. J. Am. Chem. Soc. 1983, 105, 1072. For a synthesis of Crabtree's catalyst, see: Crabtree, R. H.; Morehouse, S. M. Inorganic Syntheses; Shreeve, J. M., Ed.; Wiley: New York, 1986; Vol. 24, p 173.
21. Reduction yielded a 1.1:1 mixture of 19 and epi-19. Tetralone 20 exhibited spectral data identical to the reported values; see ref 1d above.
22. Thompson, A. S.; Humphrey, G. R.; DeMarco, A. M.; Mathre, D. J.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 5886.