Cobalt Mediated Intramolecular [2+2+2]-Cycloaddition of Enediynes Towards Linear Annelated Polycycles

Synlett

Volumn , Issue 14, 2003, Pages 2188-2192

  Eckenberg, Peter ^a   Groth, Ulrich ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Annelated polycycles; Enediynes

Indexed keywords

1,9,10 TRIHYDROXYOCTAHYDROANTHRACENE; ALKADIENE; ANTHRACENE DERIVATIVE; COBALT; DECAHYDROANTHRACENE; HEXAHYDRONAPHTHALENE; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLOADDITION; ENANTIOMER; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0344118034     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42088     Document Type: Article

References (47)

1. Transition Metal Catalyzed Reactions in Organic Synthesis, VI. For part V, see: Groth, U.; Richter, N.; Kalogerakis, A. Eur. J. Org. Chem. 2003, in print.
2. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
3. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
4. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
5. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
6. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
7. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
8. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
9. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
10. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
11. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
12. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
13. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
14. Reviews: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539; Angew. Chem. 1984, 96, 525. (b) Schore, N. E. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, L; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 1129-1162. (c) Malaska, M. J.; Vollhardt, K. P. C. Advances in Natural Product Chemistry; Atta-ur Rahman, H. E. J., Ed.; Taylor & Francis: London, 1992, 53-63. (d) Shore, N. E. Chem. Rev. 2000, 100, 1081 . (e) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; Angew. Chem. 1995, 107, 285. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (g) Malacria, M. Chem. Rev. 1996, 96, 289. (h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. (i) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901. (j) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (k) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations, Vol. 1; Lautens, M., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 439-530.
15. (a) Sternberg, E. D.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1980, 102, 4839.
16. (b) Sternberg, E. D.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 1564.
17. (c) Dunach, E.; Halterman, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 1664.
18. (d) Slowinski, F.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1999, 40, 707.
19. (e) Slowinksi, F.; Aubert, C.; Malacria, M. Eur. J. Org. Chem. 2001, 3941.
20. (a) Gadek, T. R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1981, 20, 802; Angew. Chem. 1981, 93, 801.
21. (a) Gadek, T. R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1981, 20, 802; Angew. Chem. 1981, 93, 801.
22. (b) Malacria, M.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 5010.
23. (c) Johnson, E. P.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1991, 113, 381.
24. (d) Germanas, J.; Aubert, C.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1991, 113, 4006.
25. (e) Llerena, D.; Buisine, O.; Aubert, C.; Malacria, M. Tetrahedron 1998, 54, 9373.
26. (f) Eichberg, M. J.; Dorta, R. L.; Lamottke, K.; Vollhardt, K. P. C. Org. Lett. 2000, 2, 2479.
27. (g) Eichberg, M. J.; Dorta, R. L.; Grotjahn, D. B.; Lamottke, K.; Schmidt, M.; Vollhardt, K. P. C. J. Am. Chem. Soc. 2001, 123, 9324.
28. (h) Slowinski, F.; Aubert, C.; Malacria, M. J. Org. Chem. 2003, 68, 378.
29. Chang, C. A.; King, J. A.; Vollhardt, K. P. C. J. Chem. Soc., Chem. Commun. 1981, 53.
30. (a) For similar observations see: Bradley, A.; Motherwell, W. B.; Ujjainwalla, F. Chem. Commun. 1999, 917; and references cited therein,
31. (b) Phansavath, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1998, 39, 1561.
32. (a) Stork, G.; Keitz, P. F. Tetrahedron Lett. 1989, 6981.
33. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539.
34. (c) Reviews: Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
35. (d) Fensterbank, L.; Malacria, M.; Siebuirth, S. M. Synthesis 1997, 813.
36. (e) Gauthier, D. R. J.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
37. (f) Skrydstrup, T. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, Vol. 4; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 269-291.
38. (-)-(1S)-2-Cyclohexen-1-ol (17) was prepared by enantioselective deprotonation of cyclohexene oxide according to Asami's protocol: Asami, M. Bull. Chem. Soc. Jpn. 1990, 63, 721.
39. Pohl, E.; Herbst-Irmer, R.; Groth, U.; Eckenberg, P. Acta Cryst. 1995, C51, 891.
40. Fu, P. P.; Harvey, R. G. Chem. Rev. 1978, 78, 317.
41. Kalman, J. R.; Pinkey, J. T.; Sternhall, S. Tetrahedron Lett. 1972, 5369.
42. abstract
43. Reviews: (a) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; Angew. Chem. 1986, 98, 788. (b) Krohn, K. Tetrahedron 1990, 46, 291. (c) Cambie, R. C.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1992, 45, 483.
44. Reviews: (a) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; Angew. Chem. 1986, 98, 788. (b) Krohn, K. Tetrahedron 1990, 46, 291. (c) Cambie, R. C.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1992, 45, 483.
45. Reviews: (a) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; Angew. Chem. 1986, 98, 788. (b) Krohn, K. Tetrahedron 1990, 46, 291. (c) Cambie, R. C.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1992, 45, 483.
46. Reviews: (a) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; Angew. Chem. 1986, 98, 788. (b) Krohn, K. Tetrahedron 1990, 46, 291. (c) Cambie, R. C.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1992, 45, 483.
47. (d) Lown, J. W. Chem. Soc. Rev. 1993, 22, 165.