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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 09期

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

页码：1823 / 1825

页数：3

共 52 条

[41] TOTAL SYNTHESIS OF DL-LYCORAMINE [J].

SCHULTZ, AG ;

YEE, YK ;

BERGER, MH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (24) :8065-8067

[42] ASYMMETRIC TRANSFORMATION OF EITHER ENANTIOMER OF NARWEDINE VIA TOTAL SPONTANEOUS RESOLUTION PROCESS, A CONCISE SOLUTION TO THE SYNTHESIS OF (-)-GALANTHAMINE [J].

SHIEH, WC ;

CARLSON, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5463-5465

[43]

SHIMIZU K, 1978, CHEM PHARM BULL, V26, P3765

[44]

SHIMIZU K, 1977, HETEROCYCLES, V8, P277

[45] FACILE SYNTHESIS OF (+/-)-GALANTHAMINE AND (-)-GALANTHAMINE [J].

SZEWCZYK, J ;

WILSON, JW ;

LEWIN, AH ;

CARROLL, FI .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) :195-199

[46] Enantioselective total synthesis of (-)-galanthamine [J].

Trost, BM ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (45) :11262-11263

[47]

Trost BM, 2002, ANGEW CHEM INT EDIT, V41, P2795, DOI 10.1002/1521-3773(20020802)41:15<2795::AID-ANIE2795>3.0.CO

[48]

2-2

[49] Beyond tacrine - Recently developed cholinesterase inhibitors for the treatment of Alzheimer's disease [J].

Unni, LK .

CNS DRUGS, 1998, 10 (06) :447-460

[50] SYNTHESIS OF GALANTHAMINE AND RELATED ALKALOIDS - NEW APPROACHES .1. [J].

VLAHOV, R ;

KRIKORIAN, D ;

SPASSOV, G ;

CHINOVA, M ;

VLAHOV, I ;

PARUSHEV, S ;

SNATZKE, G ;

ERNST, L ;

KIESLICH, K ;

ABRAHAM, WR ;

SHELDRICK, WS .

TETRAHEDRON, 1989, 45 (11) :3329-3345

← 1 2 3 4 5 6 →