1. Strategic approaches to the synthesis of pyrrolizidine and indolizidine alkaloids
- Author
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Alexandre V. Leontiev, Nina K. Ratmanova, Olga A. Ivanova, Igor V. Trushkov, Ivan A. Andreev, Daria Momotova, and Anton M. Novoselov
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Chemistry ,Alkene ,Stereochemistry ,Organic Chemistry ,Indolizidine ,Sigmatropic reaction ,010402 general chemistry ,Metathesis ,01 natural sciences ,Biochemistry ,Cycloaddition ,0104 chemical sciences ,chemistry.chemical_compound ,Chiral pool synthesis ,Drug Discovery ,Pyrrolizidine ,Retrosynthetic analysis - Abstract
The principal methods for the synthesis of pyrrolizidine and indolizidine alkaloids and their unnatural analogs are described. Six main “strategic” approaches in regard to a key step forming azabicyclic skeleton are identified. Namely, these are: 1) hydrogenation of the corresponding heteroaromatic compounds; 2) various condensations of carbonyl compounds and their surrogates; 3) cycloaddition reactions; 4) sigmatropic shifts and other rearrangements; 5) transition metal-mediated cyclizations (including the ring-closing alkene metathesis); and 6) radical processes. Such important issues, as retrosynthetic analysis, chiral pool synthesis, and chiral auxiliaries, are also discussed.
- Published
- 2020