Total synthesis of (±)-galanthamine from GABA through regioselective aryne insertion

被引：23

作者：

Venkatesh, Telugu ^{[1
,2
]}

Mainkar, Prathama S. ^{[1
,2
]}

Chandrasekhar, Srivari ^{[1
,2
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Dept Organ Synth & Proc Chem, Hyderabad 500007, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110020, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 08期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; (-)-GALANTHAMINE; (-)-LYCORAMINE; CYCLOADDITION;

D O I：

10.1039/c8ob03123a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+/-)-galanthamine is achieved in similar to 5% overall yield using a key regioselective aryne insertion reaction into a GABA (gamma-amino butyric acid) derivative. The strategy presented involves only two sub-critical temperature reactions and less than five chromatographic purifications to achieve the synthesis of galanthamine.

引用

页码：2192 / 2198

页数：7

共 50 条

[1] MODIFIED TOTAL SYNTHESIS OF (+-)-GALANTHAMINE THROUGH PHENOL OXIDATION
KAMETANI, T
YAMAKI, K
YAGI, H
FUKOMUTO, K
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (08): : 425 - &
[2] Total synthesis of (±)-galanthamine
Hu, XD
Tu, YO
Zhang, E
Gao, SH
Wang, SH
Wang, AX
Fan, CA
Wang, M
ORGANIC LETTERS, 2006, 8 (09) : 1823 - 1825
[3] TOTAL SYNTHESIS OF (+)- AND (-)-GALANTHAMINE
Kato, Tomoaki
Tanimoto, Hiroki
Yamada, Hisako
Chida, Noritaka
HETEROCYCLES, 2010, 82 (01) : 563 - 579
[4] Formal Total Synthesis of (±)-Cephalotaxine and Congeners via Aryne Insertion Reaction
Gouthami, Pashikanti
Chegondi, Rambabu
Chandrasekhar, Srivari
ORGANIC LETTERS, 2016, 18 (09) : 2044 - 2046
[5] An efficient total synthesis of (±)-galanthamine
Guillou, C
Beunard, JL
Gras, E
Thal, C
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (24) : 4745 - +
[6] Enantioselective total synthesis of (-)-galanthamine
Trost, BM
Toste, FD
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (45) : 11262 - 11263
[7] ORGN 274-Total synthesis of galanthamine by a tandem aryne [2+2] cycloaddition-rearrangement strategy
Buszekk, Keith R.
Bixby, Dale L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[8] Aryne Insertion Reactions Leading to Bioactive Fused Quinazolinones: Diastereoselective Total Synthesis of Cruciferane
Vaidya, Sagar D.
Argade, Narshinha P.
ORGANIC LETTERS, 2013, 15 (15) : 4006 - 4009
[9] Thioxanthone Synthesis from Thioureas through Double Aryne Insertion into a Carbon-Sulfur Double Bond
Kawada, Mayu
Tabata, Shinya
Hoshi, Yukitaka
Yoshida, Suguru
ORGANIC LETTERS, 2025, 27 (03) : 827 - 832
[10] Total synthesis of (+)-galanthamine starting from D-glucose
Tanimoto, Hiroki
Kato, Tornoaki
Chida, Noritaka
TETRAHEDRON LETTERS, 2007, 48 (36) : 6267 - 6270

← 1 2 3 4 5 →