Title:
METHOD FOR PREPARING GALANTHAMINE, DERIVATIVE THEREOF AND INTERMEDIATE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/221022
Kind Code:
A1
Abstract:
Disclosed in the present invention are intermediate I and intermediate II which have structural formulas as represented by formula (I) and formula (II), respectively, and can be used for preparing galantamine, and a preparation method therefor, and a method for the asymmetric total synthesis of galantamine and a derivative thereof with a short synthetic route and a high yield. According to the present invention, the intermediates required for the preparation of galantamine and the derivative thereof, i.e., the intermediates as represented by formula (I) and formula (II), are synthesized in sequence by means of using the simple, cheap and readily available compound 2, tert-butyl vinylcarbamate and 3-hydroxy-2-iodo-4-methoxybenzaldehyde as starting materials, and performing multiple reactions, such as a Suzuki cross-coupling reaction and a Mitsunobu reaction, and galantamine and the derivative thereof are then prepared by means of using the intermediates. The methods provided in the present invention for preparing galantamine, the derivative thereof and the intermediate thereof have a short synthesis route and a high yield, and large-scale production is easily achieved.
Inventors:
WHITE LORENZO VALENTINO (AU)
BANWELL MARTIN GERHARDT (AU)
LAN PING (CN)
HE YUTAO (CN)
HU NAN (CN)
BANWELL MARTIN GERHARDT (AU)
LAN PING (CN)
HE YUTAO (CN)
HU NAN (CN)
Application Number:
PCT/CN2022/093756
Publication Date:
November 23, 2023
Filing Date:
May 19, 2022
Export Citation:
Assignee:
UNIV JINAN (CN)
International Classes:
C07D491/107
Foreign References:
| CN102180886A | 2011-09-14 | |||
| CN101239983A | 2008-08-13 |
Other References:
PARSONS, PHILIP J. ET AL.: "A General Approach to the Galanthamine Ring System", TETRAHEDRON LETTERS, vol. 42, no. 11, 31 December 2002 (2002-12-31), XP004229239, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(01)00111-3
ENDOMA-ARIAS, MARY A. A. ET AL.: "Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate", CHEMISTRY A EUROPEAN JOURNAL, vol. volume 22, no. 41, 9 August 2016 (2016-08-09), XP071879577, ISSN: 0947-6539, DOI: 10.1002/chem.201603735
TROST, BARRY M. ET AL.: "Divergent Enantioselective Synthesis of (-)-Galanthamine and (-)-Morphine", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, 24 September 2005 (2005-09-24), XP093087577, ISSN: 0002-7863
ENDOMA-ARIAS, MARY A. A. ET AL.: "Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate", CHEMISTRY A EUROPEAN JOURNAL, vol. volume 22, no. 41, 9 August 2016 (2016-08-09), XP071879577, ISSN: 0947-6539, DOI: 10.1002/chem.201603735
TROST, BARRY M. ET AL.: "Divergent Enantioselective Synthesis of (-)-Galanthamine and (-)-Morphine", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, 24 September 2005 (2005-09-24), XP093087577, ISSN: 0002-7863
Attorney, Agent or Firm:
GUANGZHOU HUIHANG PATENT AGENCY (GENERAL PARTNERSHIP) (CN)
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