Journal
TETRAHEDRON
Volume 76, Issue 14, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131031
Keywords
Pyrrolizidine alkaloids; Indolizidine alkaloids; Organic synthesis strategies; Retrosynthetic analysis
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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. (C) 2020 Elsevier Ltd. All rights reserved.
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