Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids

被引：19

作者：

Banwell, Martin G. ^{[1
]}

Gao, Nadia ^{[1
]}

Schwartz, Brett D. ^{[1
]}

White, Lorenzo V. ^{[1
]}

机构：

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

来源：

ALKALOID SYNTHESIS | 2012年 / 309卷

关键词：

Alkaloids; Amabiline; Amaryllidaceae; Aspidospermidine; Brunsvigine; Colchicine; Corey-Winter reaction; Cross-coupling; Cyclopropane; Erythramine; Eschenmoser-Claisen rearrangement; epi-Maritinamine; Galanthamine; Grandirubrine; Haemultine; Imerubrine; Ireland-Claisen rearrangement; gamma-Lycorane; Lycoricidine; Maritinamine; Mitsunobu reaction; Nangustine; Narciclasine; Overman rearrangement; Pancracine; Pictet-Spengler reaction; Radical cyclisation; Rhazinal; Rhazinilam; Suzuki-Miyaura reaction; Ullmann reaction; Wittig reaction; CHEMOENZYMATIC TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESES; REGIOCONTROLLED TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; GEM-DIHALOCYCLOPROPANES; BIOLOGICAL EVALUATION; SCELETIUM ALKALOIDS; MONTANINE ALKALOIDS; ENT-NARCICLASINE; BUILDING-BLOCKS;

D O I：

10.1007/128_2011_217

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The total syntheses of a wide range of terrestrially derived alkaloids, especially ones isolated from members of the Amaryllidaceae family, are described. Two recurring themes associated with these syntheses are the use of two types of building blocks, namely ring-fused cyclopropanes, especially geminally-dihalogenated ones, and enzymatically derived cis-1,2-dihydrocatechols. These have often served as precursors to 2- or 3-halogenated 2-cyclohexen-1-ols that are themselves engaged in cross-coupling reactions, radical addition-elimination processes and/or Claisen- or Overman-type rearrangements so as to construct the highly functionalized six-membered rings associated with the target alkaloids.

引用

页码：163 / 202

页数：40

共 50 条

[31] Relative expression of putative genes involved in galanthamine and other Amaryllidaceae alkaloids biosynthesis in Narcissus field and in vitro tissues [J].

Aleya, Ferdausi ;

Xianmin, Chang ;

Anthony, Hall ;

Meriel, Jones .

GENE, 2021, 774

[32] Amaryllidaceae alkaloids with anti-Trypanosoma cruzi activity [J].

Martinez-Peinado, Nieves ;

Cortes-Serra, Nuria ;

Torras-Claveria, Laura ;

Pinazo, Maria-Jesus ;

Gascon, Joaquim ;

Bastida, Jaume ;

Alonso-Padilla, Julio .

PARASITES & VECTORS, 2020, 13 (01)

[33] Amaryllidaceae Family Alkaloids as Potential Drugs for Cancer Treatment [J].

Dalecka, Marketa ;

Havelek, Radim ;

Kralovec, Karel ;

Bruckova, Lenka ;

Cahlikova, Lucie .

CHEMICKE LISTY, 2013, 107 (09) :701-708

[34] A General Electro-Synthesis Approach to Amaryllidaceae Alkaloids [J].

Pollok, Dennis ;

Grossmann, Luca M. ;

Behrendt, Torsten ;

Opatz, Till ;

Waldvogel, Siegfried R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (50)

[35] Amaryllidaceae alkaloids with anti-Trypanosoma cruzi activity [J].

Nieves Martinez-Peinado ;

Nuria Cortes-Serra ;

Laura Torras-Claveria ;

Maria-Jesus Pinazo ;

Joaquim Gascon ;

Jaume Bastida ;

Julio Alonso-Padilla .

Parasites & Vectors, 13

[36] Synthetic Studies toward the Myrioneuron Alkaloids [J].

Aquilina, Jake M. ;

Smith, Myles W. .

SYNTHESIS-STUTTGART, 2023, 55 (22) :3725-3736

[37] Synthetic studies related to the akuammiline alkaloids [J].

Llopart, CC ;

Joule, JA .

ARKIVOC, 2004, :20-38

[38] Advances in the Chemical and Biological Characterization of Amaryllidaceae Alkaloids and Natural Analogues Isolated in the Last Decade [J].

Masi, Marco ;

Di Lecce, Roberta ;

Cimmino, Alessio ;

Evidente, Antonio .

MOLECULES, 2020, 25 (23)

[39] Apoptosis-inducing effects of distichamine and narciprimine, rare alkaloids of the plant family Amaryllidaceae [J].

Nair, Jerald J. ;

Rarova, Lucie ;

Strnad, Miroslav ;

Bastida, Jaume ;

van Staden, Johannes .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (19) :6195-6199

[40] Alkaloids from some species of amaryllidaceae [J].

Evidente, A .

FLAVOUR AND FRAGRANCE CHEMISTRY, 2000, 46 :109-114

← 1 2 3 4 5 →