A First Generation Chemoenzymatic Synthesis of (+)-Galanthamine

被引：28

作者：

Banwell, Martin G. ^{[1
]}

Ma, Xinghua ^{[1
]}

Karunaratne, Ochitha P. ^{[1
]}

Willis, Anthony C. ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2010年 / 63卷 / 10期

基金：

澳大利亚研究理事会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; AMARYLLIDACEAE ALKALOIDS; SECONDARY ALCOHOLS; PHENOL OXIDATION; (-)-GALANTHAMINE; GALANTHAMINE; BIOSYNTHESIS; RESOLUTION; (+/-)-GALANTHAMINE; INHIBITORS;

D O I：

10.1071/CH10201

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A total synthesis of (+)-galanthamine [(+)-1] has been achieved using the readily available and enantiomerically pure metabolite 2 as starting material. The quaternary carbon centre (C8a) associated with target 1 was constructed using the Eschenmoser-Claisen rearrangement reaction.

引用

页码：1437 / 1447

页数：11

共 44 条

[1] Effective countermeasure against poisoning by organophosphorus insecticides and nerve agents [J].

Albuquerquet, Edson X. ;

Pereira, Edna F. R. ;

Aracava, Yasco ;

Fawcett, William P. ;

Oliveira, Maristela ;

Randall, William R. ;

Hamilton, Tracey A. ;

Kan, Robert K. ;

Romano, James A., Jr. ;

Adler, Michael .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (35) :13220-13225

[2] ENANTIOSELECTIVE BACTERIAL BIOTRANSFORMATION ROUTES TO CIS-DIOL METABOLITES OF MONOSUBSTITUTED BENZENES, NAPHTHALENE AND BENZOCYCLOALKENES OF EITHER ABSOLUTE-CONFIGURATION [J].

ALLEN, CCR ;

BOYD, DR ;

DALTON, H ;

SHARMA, ND ;

BRANNIGAN, I ;

KERLEY, NA ;

SHELDRAKE, GN ;

TAYLOR, SC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :117-118

[3] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[4] Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors [J].

Banwell, MG ;

Edwards, AJ ;

Harfoot, GJ ;

Jolliffe, KA ;

McLeod, MD ;

McRae, KJ ;

Stewart, SG ;

Vögtle, M .

PURE AND APPLIED CHEMISTRY, 2003, 75 (2-3) :223-229

[5] Regio- and stereo-chemical outcomes in the nucleophilic ring-cleavage reactions of mono-epoxides derived from cis-1,2-dihydrocatechols [J].

Banwell, MG ;

Haddad, N ;

Hudlicky, T ;

Nugent, TC ;

Mackay, MF ;

Richards, SL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12) :1779-1791

[6] PHENOL OXIDATION AND BIOSYNTHESIS .5. SYNTHESIS OF GALANTHAMINE [J].

BARTON, DHR ;

KIRBY, GW .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAR) :806-&

[7] PHENOL OXIDATION AND BIOSYNTHESIS .6. BIOGENESIS OF AMARYLLIDACEAE ALKALOIDS [J].

BARTON, DHR ;

TAYLOR, JB ;

KIRBY, GW ;

THOMAS, GM .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (SEP) :4545-&

[8] N-alkylated galanthamine derivatives:: Potent acetylcholinesterase inhibitors from Leucojum aestivum [J].

Berkov, Strahil ;

Codina, Carles ;

Viladomat, Francesc ;

Bastida, Jaume .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (07) :2263-2266

[9] CRYSTALS version 12: software for guided crystal structure analysis [J].

Betteridge, PW ;

Carruthers, JR ;

Cooper, RI ;

Prout, K ;

Watkin, DJ .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2003, 36 :1487-1487

[10] STRUCTURE AND BIOSYNTHESIS OF CHLIDANTHINE [J].

BHANDARK.JG ;

KIRBY, GW .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (09) :1224-&

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