The 3,3'-pyrrolidinyl-spirooxindole unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties. Significant recent advances in the synthesis of this fused heterocyclic system have led to intense interest in the development of related compounds as potential medicinal agents or biological probes.

Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

https://chemistry.mdma.ch/hiveboard/rhodium/pdf/archive/merbst/quinoline1999.pdf

Quinoline, quinazoline and acridone alkaloids

The preparation of urea by Wöhler constituted a landmark achievement in organic chemistry, and it laid the ground for the early days of target-oriented organic synthesis.1 Since then, significant progress has been achieved in this discipline; many powerful single bond forming reactions and asymmetric variants have been developed. These discoveries have paved the way for the stereoselective assembly of complex organic molecules, a task deemed inconceivable by early practitioners. A great many strategies were invented by chemists in order to facilitate the synthesis of complex natural products.2 One avenue in emulating nature’s efficiency would * To whom correspondence should be addressed. E-mail: dennis.hall@ ualberta.ca. † Novartis Institute for Biomedical Research. ‡ Department of Chemistry, University of Alberta. Chem. Rev. 2009, 109, 4439–4486 4439

Natural product synthesis using multicomponent reaction strategies.

Isatins As Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks

Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids

A new glucosidic lupin-alkaloid, (-)-(trans-4'-β-D-glucopyranosyloxycinnamoyl)-lupinine (5), was newly isolated from the fresh seedings of Lupinus luteus. Its structure has been confirmed by direct comparison with a synthetic material. The concentration of 5 in the immature and mature seeds of L. luteus was negligibly low, but its concentration increased rapidly during the first 3-10 day's growth of seedlings and became a minor component again in the later stages of the plant's growth.

(-)-(trans-4'-β-D-Glucopyranosyloxycinnamoyl) lupinine, a New Lupin Alkaloid in Lupinus Seedlings

Gardneramine, the main alkaloid of Gardneria spp (Loganiaceae), was found to have the structure I At the same time a minor base, alkaloid G, was elucidated to be 18-demethylgardneramine (XVIII) Both alkaloids have an iminoether ring as the masked oxindole, some novel reactivities of which are described Three trimethoxy oxindoles (XXXII a, b, c) were synthesized as the model compounds for locating the aromatic substituents of I

Structure of Gardneramine and 18-Demethylgardneramine

Alkaloids of Hernandia ovigera L. IV. The constituents of Hernandia ovigera L. collected in the Bonin Islands

Lupin alkaloids from flowers of Echinosophora koreensis

Cytisine N-methyltransferase, a new enzyme catalyzing the formation of N-methyl-cytisine (II) from cytisine (I) and S-adenosyl-L-methionine, was found in the seedlings of Thermopsis species. 5-Methyltetrahydrofolic acid did not act as a methyl donor for the N-methylation of cytisine. A magnesium cation dependency was not detected. Some other properties of the enzyme are also described.

An S-Adenosyl-L-methionine : Cytisine Methyltransferase in Thermopsis Seedlings

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