Novel asymmetric synthesis of a bicyclo[3.1.0]hexane derivative by an efficient retro-Diels-Alder strategy

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8637-8640

  Moher, Eric D ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CYCLOHEXANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

BETULACEAE;

EID: 0030602196     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02025-4     Document Type: Article

References (23)

1. 1. (a) Leeson, P. D.; Iversen, L. L. J. Med. Chem. 1994, 37, 4053.
2. (b) Chemical and Engineering News, May 13, 1996, 41.
3. 2. Monn, J. A. and Schoepp, D. D. In Recent Progress in Excitatory Amino Acid Research; McCall, Ed.; Academic Press Inc. 1994, p. 53.
4. 3. Monn, J. A.; Valli, M. J.; Massey, S. M.; Wright, R. A.; Salhoff, C. R.; Johnson, B. G.; Howe, T.; Alt, C. A.; Rhodes, G. A.; Robey, R. L.; Griffey, K. R.; Tizzano, J. P.; Kallman, M. J.; Helton, D. R.; Schoepp, D. D. manuscript in preparation for J. Med. Chem.
5. 4. cf. Payne, G. B. J. Org. Chem. 1967, 32, 3351.
6. 5. For reviews see: (a) Ripoll, J. L.; Rouessac, A.; Rouessac, F. Tetrahedron 1978, 34, 19.
7. (b) Ichihara A. Synthesis 1987, 207.
8. 6. For a recent example see: Takano, S.; Moriya, M.; Ogasawara, K. Tetrahedron Lett. 1992, 33, 1909 and references cited therein.
9. 7. Grieco, P. A.; Abood, N. J. Org. Chem. 1989, 54, 6008.
10. 8. cf. Stork, G.; Nelson, G. L.; Rouessac, F.; Olivier, G. J. Am. Chem. Soc. 1971, 93, 3091.
11. 9. (a) For a review of the vinylcyclopropane/cyclopentene rearrangement see: Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
12. (b) For an interesting example of a tandem retro-Diels-Alder/vinylcyclopropane rearrangement under FVP conditions see: Trost, B. M.; Parquette, J. R. J. Org. Chem. 1994, 59, 7568.
13. 10. (a) Klunder, A. J. H.; Huizinga, W. B.; Hulsof, A. J. M.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543.
14. (b) Garland, R. B.; Miyano, M.; Pireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854.
15. (c) Takano, S.; Inomota, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636.
16. 11. Doyle, M. P.; Bagheri, V.; Wandless, T. J.; Harn, N. K.; Brinker, D. A.; Eagle, C. T.; Loh, K.-L. J. Am. Chem. Soc. 1990, 112, 1906. For a recent review of the intra-molecular cyclopropanation see: Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
17. 11. Doyle, M. P.; Bagheri, V.; Wandless, T. J.; Harn, N. K.; Brinker, D. A.; Eagle, C. T.; Loh, K.-L. J. Am. Chem. Soc. 1990, 112, 1906. For a recent review of the intra-molecular cyclopropanation see: Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
18. 12. Doyle, M. P.; Dorow, R. L.; Tamblyn, W. H. J. Org. Chem. 1982, 47, 4059. For a report describing the Pd(II)-catalyzed cyclopropanation of electron deficient alkenes see: Majchrzak, M. W.; Kotelko, A.; Lambert, J. B. Synthesis, 1983, 469.
19. 12. Doyle, M. P.; Dorow, R. L.; Tamblyn, W. H. J. Org. Chem. 1982, 47, 4059. For a report describing the Pd(II)-catalyzed cyclopropanation of electron deficient alkenes see: Majchrzak, M. W.; Kotelko, A.; Lambert, J. B. Synthesis, 1983, 469.
20. 13C NMR, and IR spectra consistent with their assigned structure. All intermediates have exhibited satisfactory (±0.4%) elemental analysis.
21. 14. Chiralpak® AD column (4.6 mm × 250 mm) eluting with 30% n-PrOH/hexanes at a flow rate of 1 ml/min and UV detection at 220 or 230 nm.
22. 15. Zorbax® SB-Phenyl column (4.6 mm × 250 mm) eluting with 40% acetonitrile/0.1 M sodium phosphate monobasic buffer (pH=2) at a flow rate of 1.5 ml/min with UV detection at 210 nm.
23. 3: C, 64.27; H, 7.19. Found: C, 64.10; H, 7.31.