Formal synthesis of (±)-physostigmine

Tetrahedron

Volumn 52, Issue 15, 1996, Pages 5339-5348

  Morales Ríos, Martha S ^a   Bucio, María A ^a   Joseph Nathan, Pedro ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

PHYSOSTIGMINE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029872818     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00176-7     Document Type: Article

References (26)

1. For reviews, see (a) Takano, S.; Ogasawara, K. The Alkaloids; Brossi, A., Ed.; Academic Press; New York, 1989, 36, 225. (b) Robinson, B. The Alkaloids; Manske, R.H.F., Ed; Academic Press; New York, 1968, 10, 398 and 13, Chapter 4.
2. For reviews, see (a) Takano, S.; Ogasawara, K. The Alkaloids; Brossi, A., Ed.; Academic Press; New York, 1989, 36, 225. (b) Robinson, B. The Alkaloids; Manske, R.H.F., Ed; Academic Press; New York, 1968, 10, 398 and 13, Chapter 4.
3. Carlé, J.S.; Christophersen, C. J. Org. Chem. 1980, 45, 1586-1589.
4. (a) Morales-Ríos, M.S.; Bucio, M.A.; Joseph-Nathan, P. Tetrahedron Lett. 1994, 35, 881-882.
5. (b) Morales-Rios, M.S.; Bucio, M.A.; García-Martínez, C.; Joseph-Nathan, P. Tetrahedron Lett. 1994, 35, 6087-6088.
6. (a) Julian, P.L.; Pikl, J.; Boggess, D. J. Am. Chem. Soc.., 1934, 56, 1797-1801.
7. (b) Julian, P.L.; Pikl, J. J. Am. Chem. Soc., 1935, 57, 539-544 and 563-566.
8. (c) Schönenberger, B.; Brossi, A. Helv. Chim. Acta, 1986, 69, 1486-1487.
9. (d) Yu, Q.-S.; Brossi, A.; Heterocycl., 1988, 27, 745-750 and 1709-1712.
10. (d) Lee, T.B.K.; Wong, G.S.K. J. Org. Chem., 1991, 56, 872-875.
11. Morales-Ríos, M.S.; Bucio-Vásquez, M.A.; Joseph-Nathan, P. J. Heterocycl. Chem., 1993, 30, 953-956.
12. 000 = 639.89, λ = 1.54178Å, scan type θ-2θ, scan speed variable 4.0 - 29.3, scan limits 3° ≥ 2θ ≥ 110° of the 2166 collected reflections, 1489 [I = 3σ(I)] were considered as observed. The structure was refined to R = 6.65% using 1355 independent reflections. Atomic coordinates, bond lenghts, bond angles, anisotropic thermal parameters, hydrogen coordinates, calculated and observed structure factors and torsion angles are deposited at the Cambridge Crystallographic Data Centre.
13. (a) Swiss, K.A.; Hinkley, W.; Maryanoff, C.A.; Liotta, D.C. Synthesis, 1992, 127-131 and references contained therein.
14. (b) Yamamoto, Y.; Nishii, S.; Ibuka, T. J. Chem. Soc. Chem. Commun. 1987, 464-466.
15. (c) Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc. Chem. Commun., 1989, 31-33.
16. (d) Chérest, M.; Felkin, H.; Frajerman, C.; Lion, C.; Roussi, G.; Swierczewski, G. Tetrahedron Lett. 1966, 875-879.
17. (a) Rees, C.W.; Sabet, C.R. J. Chem. Soc., 1965, 870-875.
18. (b) Buchardt, O.; Lohse, C. Tetrahedron Lett. 1966, 4355-4361.
19. (c) Buchardt, O.; Kumler, P. L.; Lohse, C. Acta Chem. Scand., 1969, 23, 1155-1167.
20. (d) Harrison, D.M. Tetrahedron Lett. 1984, 25, 6063-6064.
21. Morales-Rios, M.S.; Bucio, M.A.; Joseph-Nathan, P. Magn. Reson. Chem. 1993, 31, 960-962.
22. Brown, H.C.; Garg, C.P.; Liu, K.-T. J. Org. Chem., 1971, 36, 387-390.
23. Krapcho, A.P. Synthesis, 1982, 805-822 and 893-914.
24. Morales-Rios, M.S.; Joseph-Nathan, P. Magn. Reson. Chem., 1987, 25, 911-918.
25. 2Me) ppm correlate with the methyl singlets at 3.84 and 3.82 ppm, respectively.
26. Robinson, B. J. Chem. Soc. 1965, 3336-3339.