Total synthesis of (±)-galanthamine

被引:68
作者
Hu, XD [1 ]
Tu, YO
Zhang, E
Gao, SH
Wang, SH
Wang, AX
Fan, CA
Wang, M
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China
关键词
D O I
10.1021/ol060339b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient total synthesis of (+/-)-galanthamine was achieved from commercially available materials through a novel approach, in which the construction of its core structure and the special allylic alcohol group were based on a successive semipinacol rearrangement/desilyation/cyclization and Saegusa-Ito oxidation, respectively.
引用
收藏
页码:1823 / 1825
页数:3
相关论文
共 52 条
[1]   USE OF THE ELECTROPHILIC ARYLATION REACTION OF ARYL-LEAD TRIACETATES IN A SYNTHESIS OF (+/-)-LYCORAMINE [J].
ACKLAND, DJ ;
PINHEY, JT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2695-2700
[2]   RECENT APPLICATIONS OF THE SHAPIRO REACTION [J].
ADLINGTON, RM ;
BARRETT, AGM .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (02) :55-59
[3]   PHENOL OXIDATION AND BIOSYNTHESIS .5. SYNTHESIS OF GALANTHAMINE [J].
BARTON, DHR ;
KIRBY, GW .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAR) :806-&
[4]   VINYL-LITHIUM REAGENTS FROM ARENESULFONYLHYDRAZONES [J].
CHAMBERLIN, AR ;
STEMKE, JE ;
BOND, FT .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :147-154
[5]   A concise, scaleable synthesis of narwedine [J].
Chaplin, DA ;
Fraser, N ;
Tiffin, PD .
TETRAHEDRON LETTERS, 1997, 38 (45) :7931-7932
[6]   New kilogram-synthesis of the anti-Alzheimer drug (-)-galanthamine [J].
Czollner, L ;
Frantsits, W ;
Küenburg, B ;
Hedenig, U ;
Fröhlich, J ;
Jordis, U .
TETRAHEDRON LETTERS, 1998, 39 (15) :2087-2088
[7]   An efficient total synthesis of (±)-lycoramine [J].
Fan, CA ;
Tu, YQ ;
Song, ZL ;
Zhang, E ;
Shi, L ;
Wang, M ;
Wang, BM ;
Zhang, SY .
ORGANIC LETTERS, 2004, 6 (25) :4691-4694
[8]   Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications [J].
Giacobini, E .
NEUROCHEMISTRY INTERNATIONAL, 1998, 32 (5-6) :413-419
[9]   The complex of a bivalent derivative of galanthamine with torpedo acetylcholinesterase displays drastic deformation of the active-site gorge:: Implications for structure-based drug design [J].
Greenblatt, HM ;
Guillou, C ;
Guénard, D ;
Argaman, A ;
Botti, S ;
Badet, B ;
Thal, C ;
Silman, I ;
Sussman, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15405-15411
[10]   SYNTHETIC STUDIES ON QUASSINOIDS - TOTAL SYNTHESIS OF (+/-)-CHAPARRINONE [J].
GROSS, RS ;
GRIECO, PA ;
COLLINS, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9436-9437