Indolizidine and quinolizidine alkaloids

Abstract

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids from microbial, plant and animal sources. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including ants, amphibians and beetles; ipalbidine, phenanthroindolizidines and related alkaloids; Lycopodium alkaloids; lupine alkaloids; and alkaloids from bacterial and marine sources. The literature from July 2002 to June 2003 is reviewed, and 174 references are cited.

Synthesis of Alkaloid Analogues from α‐Amino Acids by One‐Pot Radical Decarboxylation/Alkylation

“…[2] However, they also have important sideeffects or limited bioavailability. In order to overcome these problems, different synthetic analogues have been developed.…”

“…[1] The antitumour agent swainsonine [2] (Figure 1), the non-addictive analgesic ipalbidine [3] and the poisonous histrionicotoxin [4] exemplify the variety of structures and biological activities. In order to study structure-activity relationships (SAR) many alkaloid analogues have been prepared, and in many cases new synthetic strategies have been developed.…”

Transition Metal‐Catalyzed Synthesis of Fused Five‐Membered Aromatic Heterocycles

“…The diverse pharmacological potential of indolizines and related derivatives stimulates a continuous interest in utilizing molecules containing this core in synthetic biologically active compounds [279][280][281][282][283][284][285][286][287]. Furthermore, indolizines, due to their intriguing molecular properties, found applications in the field of material science and in a range of artificial materials [279,280].…”

Creation of quaternary stereocentres: synthesis of new polyhydroxylated indolizidines

“…1 Furthermore, a wide range of structural analogues have also been synthesized to be evaluated as selective inhibitors and potential therapeutic agents. 2 However, among these synthetic hydroxylated indolizidines, only a few structures contain a quaternary carbon at the a-position to the nitrogen at the ring junction. [3][4][5][6][7][8] The methodologies developed for their construction include the creation of the quaternary centre by C-C bond formation through alkylation 3 and aldol 4 reactions of tert-butyl a-aminoester derivatives, or through nucleophilic addition to N-acyliminium ions.…”