ENANTIOSELECTIVE SYNTHESIS OF (-)-PHYSOSTIGMINE
The first enantioselective synthesis of (-)-physostigmine (1), a potent cholinesterase-inhibiting alkaloid from Physostigma venenosum Balf., has been accomplished using (S)-(-)-benzyl 2, 3-epoxypropyl ether (5) as a chiral synthon.
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| Published in | Chemical & pharmaceutical bulletin Vol. 30; no. 7; pp. 2641 - 2643 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
The Pharmaceutical Society of Japan
01.01.1982
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0009-2363 1347-5223 |
| DOI | 10.1248/cpb.30.2641 |
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| Abstract | The first enantioselective synthesis of (-)-physostigmine (1), a potent cholinesterase-inhibiting alkaloid from Physostigma venenosum Balf., has been accomplished using (S)-(-)-benzyl 2, 3-epoxypropyl ether (5) as a chiral synthon. |
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| AbstractList | The first enantioselective synthesis of (-)-physostigmine (1), a potent cholinesterase-inhibiting alkaloid from Physostigma venenosum Balf., has been accomplished using (S)-(-)-benzyl 2, 3-epoxypropyl ether (5) as a chiral synthon. |
| Author | Goto, Emiko Takano, Seiichi Hirama, Michiyasu Ogasawara, Kunio |
| Author_xml | – sequence: 1 fullname: Takano, Seiichi – sequence: 1 fullname: Ogasawara, Kunio – sequence: 1 fullname: Goto, Emiko – sequence: 1 fullname: Hirama, Michiyasu |
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| CitedBy_id | crossref_primary_10_1246_cl_1991_57 crossref_primary_10_1016_S0040_4039_01_02138_4 crossref_primary_10_1021_ol006065o crossref_primary_10_1002_chem_201001451 crossref_primary_10_1016_S0040_4039_00_01471_4 crossref_primary_10_1021_ol302388t crossref_primary_10_1021_acs_orglett_5b03082 crossref_primary_10_3987_COM_04_10041 crossref_primary_10_1246_cl_1984_949 crossref_primary_10_1016_j_tetlet_2009_03_012 crossref_primary_10_1016_S0957_4166_00_80490_5 crossref_primary_10_1039_c2cc33129b crossref_primary_10_1021_ol503766y crossref_primary_10_1016_S0040_4020_01_87445_7 crossref_primary_10_1039_b316241a crossref_primary_10_1016_S0957_4166_97_00119_5 crossref_primary_10_1016_j_tetasy_2008_09_021 crossref_primary_10_1021_ol203052y crossref_primary_10_1002_hlca_19860690620 crossref_primary_10_1016_S0957_4166_99_00425_5 crossref_primary_10_1021_acs_orglett_7b00078 crossref_primary_10_1021_ol303204v crossref_primary_10_1002_ejoc_200900391 crossref_primary_10_1246_cl_1990_109 |
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| References | 10) Natural physostigmine (1) was hydrolyzed with ethanolic potassium hydroxide to give (-)-eseroline (2) which gave (-)-esermethole (3) on treatment with diazomethane. 1) Pertinent reviews: (a) E. Coxworth, "The Alkaloids," R.H.F. Manske, Edn., Vol. VIII, Academic Press, New York, 1965, p. 1. (b) B. Robinson, "The Alkaloids," R.H.F. Manske, Edn., Vol. X, Academic Press, New York, 1968, p. 383. 5) S. Takano, E. Goto, M. Hirama, and K. Ogasawara, Heterocycles, 16, 381(1981). 6) The ether (5) was used as a chiral synthon for the first enantioselective synthesis of (-)-mesembrine: see, S. Takano, Y. Imamura, and K. Ogasawara, Tetrahedron Lett., 22, 4479(1981). 4) A.K.M. Anisuzzaman and L.N. Owen, J. Chem. Soc. (C), 1967, 1021. 7) Satisfactory spectral (IR, 1H-NMR, MS) and analytical (combustion and high resolution MS) data were obtained for all new compounds. 8) Cf. F.A. Carey and R.M. Giuliano, J. Org. Chem., 46, 1366(1981). 9) Recent synthesis of racemic esermethole (3): M. Ikeda, S. Matsugashita, and Y. Tamura, J. Chem. Soc. Perkin Trans. 1, 1977, 1166. 2) Recent racemic synthesis: J.B.P.A. Wijnberg and W.N. Speckamp, Tetrahedron, 34, 2399(1978). 3) P.L. Julian and J. Pikl, J. Am. Chem. Soc., 57, 755(1935). 11) M. Polonovski and C. Nitzberg, Bull. Soc. Chim. Fr., [iv], 19, 33(1916). |
| References_xml | – reference: (b) B. Robinson, "The Alkaloids," R.H.F. Manske, Edn., Vol. X, Academic Press, New York, 1968, p. 383. – reference: 10) Natural physostigmine (1) was hydrolyzed with ethanolic potassium hydroxide to give (-)-eseroline (2) which gave (-)-esermethole (3) on treatment with diazomethane. – reference: 8) Cf. F.A. Carey and R.M. Giuliano, J. Org. Chem., 46, 1366(1981). – reference: 5) S. Takano, E. Goto, M. Hirama, and K. Ogasawara, Heterocycles, 16, 381(1981). – reference: 11) M. Polonovski and C. Nitzberg, Bull. Soc. Chim. Fr., [iv], 19, 33(1916). – reference: 2) Recent racemic synthesis: J.B.P.A. Wijnberg and W.N. Speckamp, Tetrahedron, 34, 2399(1978). – reference: 1) Pertinent reviews: (a) E. Coxworth, "The Alkaloids," R.H.F. Manske, Edn., Vol. VIII, Academic Press, New York, 1965, p. 1. – reference: 9) Recent synthesis of racemic esermethole (3): M. Ikeda, S. Matsugashita, and Y. Tamura, J. Chem. Soc. Perkin Trans. 1, 1977, 1166. – reference: 6) The ether (5) was used as a chiral synthon for the first enantioselective synthesis of (-)-mesembrine: see, S. Takano, Y. Imamura, and K. Ogasawara, Tetrahedron Lett., 22, 4479(1981). – reference: 7) Satisfactory spectral (IR, 1H-NMR, MS) and analytical (combustion and high resolution MS) data were obtained for all new compounds. – reference: 4) A.K.M. Anisuzzaman and L.N. Owen, J. Chem. Soc. (C), 1967, 1021. – reference: 3) P.L. Julian and J. Pikl, J. Am. Chem. Soc., 57, 755(1935). |
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| SubjectTerms | cholinesterase inhibitor |
| Title | ENANTIOSELECTIVE SYNTHESIS OF (-)-PHYSOSTIGMINE |
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