Enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted Diels?Alder reaction

Journal of Organic Chemistry

Volumn 75, Issue 8, 2010, Pages 2718-2721

  Weimar, Marko ^a   Dürner, Gerd ^a   Bats, Jan W ^a   Göbel, Michael W ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDER REACTIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; LEWIS ACID; TOTAL YIELD;

HYDROGEN BONDS; OLEFINS;

SYNTHESIS (CHEMICAL);

ESTRONE;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; ESTROGEN SYNTHESIS; HYDROGEN BOND; REACTION ANALYSIS;

ESTRONE; HYDROGEN BONDING; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 77950962949     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100053j     Document Type: Article

References (50)

1. Selected classical syntheses: Anner, G.; Miescher, K. Helv. Chim. Acta 1948, 31, 2173-2183
2. Ananchenko, S. N.; Torgov, I. V. Tetrahedron Lett. 1963, 4, 1553-1558
3. Rufer, C.; Schrder, E.; Gibian, H. Justus Liebigs Ann. Chem. 1967, 701, 206-216
4. Cohen, N.; Banner, B. L.; Eichel, W. F.; Parrish, D. R.; Saucy, G.; Cassal, J.-M.; Meier, W.; Frst, A. J. Org. Chem. 1975, 40, 681-685
5. Eder, U.; Gibian, H.; Haffer, G.; Neef, G.; Sauer, G.; Wiechert, R. Chem. Ber. 1976, 109, 2948-2953
6. Bartlett, P. A.; Johnson, W. S. J. Am. Chem. Soc. 1973, 95, 7501-7502
7. Selected recent syntheses: Quellet, L.; Langlois, P.; Deslongchamps, P. Synlett 1997, 689-690
8. Tietze, L. F.; Nbel, T.; Spescha, M. J. Am. Chem. Soc. 1998, 120, 8971-8977
9. Pattenden, G.; Gonzales, M. A.; McCulloch, S.; Walter, A.; Woodhead, S. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12024-12029
10. Lim, C.; Evenson, G. N.; Perrault, W. R.; Pearlman, B. A. Tetrahedron Lett. 2006, 47, 6417-6420
11. Soorukram, D.; Knochel, P. Org. Lett. 2007, 9, 1021-1023
12. Yeung, Y.-Y.; Chein, R. J.; Corey, E. J. J. Am. Chem. Soc. 2007, 129, 10346-10347
13. Herrmann, P.; Bud?ínsk, M.; Kotora, M. J. Org. Chem. 2008, 73, 6202-6206
14. Synthesis of estrogens by intramolecular Diels?Alder reactions of o -quinodimethanes: Kametani, T.; Matsumoto, H.; Nemoto, H.; Fukumoto, K. J. Am. Chem. Soc. 1978, 100, 6218-6220
15. Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1980, 102, 5253-5261
16. Oppolzer, W.; Roberts, D. A. Helv. Chim. Acta 1980, 63, 1703-1705
17. Grieco, P. A.; Takigawa, T.; Schillinger, W. J. J. Org. Chem. 1980, 45, 2247-2251
18. Ito, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1981, 103, 476-477
19. Quinkert, G.; Schwartz, U.; Stark, H.; Weber, W.-D.; Adam, F.; Baier, H.; Frank, G.; Drner, G. Liebigs Ann. Chem. 1982, 1999-2040
20. Hakuba, H.; Kitagaki, S.; Mukai, C. Tetrahedron 2007, 63, 12639-12645
21. Djuric, S.; Sarkar, T.; Magnus, P. J. Am. Chem. Soc. 1980, 102, 6885-6886
22. Nicolaou, K. C.; Barnette, W. E.; Ma, P. J. Org. Chem. 1980, 45, 1463-1470
23. Dane, E.; Schmitt, J. Liebigs Ann. Chem. 1938, 536, 196-203
24. Dane, E.; Schmitt, J. Liebigs Ann. Chem. 1939, 537, 246-249
25. Singh, G. J. Am. Chem. Soc. 1956, 78, 6109-6115
26. Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1979, 57, 3308-3319
27. Cole, J. E., Jr.; Johnson, W. S.; Robins, P. A.; Walker, J. J. Chem. Soc. 1962, 244-278
28. For more recent syntheses of estrone starting from Danes diene 1, see: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 7403-7406
29. Hu, Q.-Y.; Rege, P. D.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 5984-5986
30. Canales, E.; Corey, E. J. Org. Lett. 2008, 10, 3271-3273
31. Yates, P.; Eaton, P. J. Am. Chem. Soc. 1960, 82, 4436-4437
32. Seebach, D.; Beck, A. K.; Imwinkelried, R.; Roggo, S.; Wonnacott, A. Helv. Chim. Acta 1987, 70, 954-974
33. Quinkert, G.; Del Grosso, M.; Bucher, A.; Bats, J. W.; Drner, G. Tetrahedron Lett. 1991, 32, 3357-3360
34. Quinkert, G.; Del Grosso, M.; Bucher, A.; Bauch, M.; Dring, W.; Bats, J. W.; Drner, G. Tetrahedron Lett. 1992, 33, 3617-3620
35. Quinkert, G.; Del Grosso, M.; Dring, A.; Dring, W.; Schenkel, R. I.; Bauch, M.; Dambacher, G. T.; Bats, J. W.; Zimmermann, G.; Drner, G. Helv. Chim. Acta 1995, 78, 1345-1391
36. Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520-1543
37. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743
38. Wassermann, A. J. Chem. Soc. 1942, 618-621
39. Rubin, W.; Steiner, H.; Wassermann, A. J. Chem. Soc. 1949, 3057
40. Schuster, T.; Kurz, M.; Gbel, M. W. J. Org. Chem. 2000, 65, 1697-1701
41. Lehr, S.; Schtz, K.; Bauch, M.; Gbel, M. W. Angew. Chem., Int. Ed. 1994, 33, 984-986
42. Schuster, T.; Gbel, M. W. Synlett 1999, 966-968
43. Schuster, T.; Bauch, M.; Drner, G.; Gbel, M. W. Org. Lett. 2000, 2, 179-181
44. Diels?Alder dimerization of Danes diene: Torgov, I. V.; Nazarov, I. N. Zh. Obshch. Khim. 1959, 29, 787
45. Kuo, C. H.; Taub, D.; Wendler, N. L. J. Org. Chem. 1968, 33, 3126-2132
46. Cramer, N.; Buchweitz, M.; Laschat, S.; Frey, W.; Baro, A.; Mathieu, D.; Richter, C.; Schwalbe, H. Chem. - Eur. J. 2006, 12, 2488-2503
47. A recrystallization yield of 83% requires the original enantiomeric excess to be higher than the reported value of 81% ee. This discrepancy may be explained by a nonhomogeneous distribution of enantiomers in the solid product of 19 + ent- 19 when the sample for ee determination was taken.
48. Tsogoeva, S. B.; Drner, G.; Bolte, M.; Gbel, M. W. Eur. J. Org. Chem. 2003, 1661-1664
49. Akalay, D.; Drner, G.; Bats, J. W.; Bolte, M.; Gbel, M. W. J. Org. Chem. 2007, 72, 5618-5624
50. Catalysis by glass surfaces (or by silica gel) is known to induce a nonselective background reaction; see ref 13.