A novel total synthesis of (+)-himbacine, a potent antagonist of the muscarinic receptor of M2 subtype

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3399-3402

  Takadoi, Masanori ^a   Katoh, Tadashi ^a   Ishiwata, Akihiro ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

Alkaloids; Diels Alder reaction; Natural products; Stereocontrol

Indexed keywords

ACETYLCHOLINE; BUTENOLIDE; HIMBACINE; ISOBENZOFURAN DERIVATIVE; MUSCARINIC M2 RECEPTOR; MUSCARINIC M2 RECEPTOR ANTAGONIST; SULFONE DERIVATIVE; TETRAHYDROISOBENZOFURAN; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; DRUG SYNTHESIS; HYDROGENATION; REDUCTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 0033597147     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00473-6     Document Type: Article

References (20)

1. [1] Brown, R. F. C., Drummond, R., Fogerty, A. C., Hughes, G. K., Pinhey, J. T., Ritchie, E., Taylor, W. C., Aust. J. Chem., 1956, 9, 283.
2. [2] a) Kozikowski, A. P., Fauq, A. H., Miller, J. H., McKinney, M., Bioorg. Med. Chem. Lett., 1992, 2, 797.
3. b) Malaska, M. J., Fauq, A. H., Kozikowski, A. P., Aagaard, P. J., McKinney, M., Bioorg. Med. Chem. Lett., 1993, 3, 1247.
4. c) Malaska, M. J., Fauq, A. H., Kozikowski, A. P., Aagaard, P. J., McKinney, M., Bioorg. Med. Chem. Lett., 1995, 5, 61.
5. [3] Miller, J. H., Aagaard, P. J., Gibson, V. A., McKinney, M., J. Pharmacol. Exp. Ther., 1992, 263, 663.
6. [4] a) Hart, D. J., Wu, W.-L., Kozikowski, A. P., J. Am. Chem. Soc., 1995, 117, 9369.
7. b) Hart, D. J., Li, J., Wu, W.-L., Kozikowski, A. P., J. Org. Chem., 1997, 62, 5023.
8. [5] Chackalamannil, S., Davies, R. J., Asberom, T., Doller, D., Leone, D., J. Am. Chem. Soc., 1996, 118, 9812.
9. [6] Tochtermann, W., Bruhn, S., Wolff, C., Tetrahedron Lett., 1994, 35, 1165.
10. [7] Garst, M. E., Spencer, T. A., J. Am. Chem. Soc., 1973, 95, 250.
11. [8] a) Ito, Y., Kobayashi, Y., Kawabata, T., Takase, M., Terashima, S., Tetrahedron, 1989, 45, 5767.
12. b) Beckmann, M., Hildebrandt, H., Winterfeldt, E., Tetrahedron: A symmetry, 1990, 1, 335.
13. c) Ortuño, R. M., Alonso, D., Cardellach, J., Font, J., Tetrahedron, 1987, 43, 2191.
14. [9] Grieco, P. A., Nunes, J. J., Gaul, M. D., J. Am. Chem. Soc., 1990, 112, 4595.
15. [10] Ortuño, R. M., Batllori, R., Ballesteros, M., Monsalvatje, M., Corbera, J., Sanchez-Ferrando, F., Font, J., Tetrahedron Lett., 1987, 28, 3405.
16. [11] Brion, F., Tetrahedron Lett., 1982, 23, 5299.
17. [12] Ley, S. V., Norman, J., Griffith, W. P., Marsden, S. P., Synthesis, 1994, 639.
18. 9. Details of the X-ray analysis will be reported in a separate paper.
19. 13C-NMR, and IR) data of 2 was identical to those reported [4b].
20. 3) [4b] ] and mp. 127-128 °C (recrystallized from hexane) [authentic sample, mp. 128-129 °C (recrystallized from hexane): lit. mp. 129-130 °C [4b]]. An authentic sample of 1 was purchased from Sigma Chemical Co., Ltd., and purified by recrystallization from hexane.