Efficient synthesis of an enantiopure thiasteroid by a double heck reaction

Australian Journal of Chemistry

Volumn 57, Issue 7, 2004, Pages 635-640

  Tietze, Lutz F ^a   Lücke, Lars P ^a   Major, Felix ^a   Müller, Peter ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; DERIVATIVES; HYDROGENATION; ISOMERIZATION; MOLECULAR DYNAMICS; OLEFINS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

BIOLOGICAL ACTIVITIES; CROSS COUPLING REACTIONS; ESTROGENS; HECK REACTIONS;

ORGANIC COMPOUNDS;

EID: 3242689079     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH04034     Document Type: Article

References (50)

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12. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
13. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
14. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
15. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
16. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
17. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
18. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
19. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
20. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
21. Total syntheses of steroids: (a) X. Jiang, D. F. Covey, J. Org. Chem. 2002, 67, 4893. doi:10.1021/J0025535K (b) W. Yu, Z. Jin, J. Am. Chem. Soc. 2002, 124, 6576. doi: 10.1021/JA012119T (c) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843. doi:10.1016/S0040-4039(00)02118-3 (d) D. Fortin, F. Gaudette, E. Marsault, P. Deslongchamps, Tetrahedron 2001, 57, 4167. doi: 10.1016/80040-4020(01)00290-3 (e) W. S. Johnson, W. R. Bartlett, B. A. Czeskis, A. Gautier, C. H. Lee, R. Lemoine, E. J. Leopold, G. R. Luedtke, K. J. Bancroft, J. Org. Chem. 1999, 64, 9587. doi: 10.1021/J0991196S (f) L. Quellet, P. Langlois, P. Deslongchamps, Synlett 1997, 689. (g) G. Quinkert, M. del Grosso, A. Döring, W. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, et al., Helv. Chim. Acta 1995, 78, 1345. (h) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962. (i) T. Takahashi, K. Shimizu, T. Doi, J. Tsuji, Y. Fukazawa, J. Am. Chem. Soc. 1988, 110, 2674. (j) S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. (k) K. P. C. Vollhardt, in Strategies and Tactics in Organic Synthesis (Ed. T. Lindberg) 1984, pp. 299-324 (Academic Press: Orlando, FL). (l) T. Kametani, H. Nemoto, Tetrahedron 1981, 37, 3. doi: 10.1016/50040-4020(01)97707-5
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50. Crystallographic data (excluding structure factors) for the structure of 7 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-230286. Copies of the data can be obtained free of charge on application to the CCDC (e-mail: deposit@ccdc.cam.ac.uk).