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

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