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Title: Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
Author: Yayik, Nihan
Pérez Bosch, Maria
Molins i Grau, Elies
Bosch Cartes, Joan
Amat Tusón, Mercedes
Keywords: Alcaloides
Compostos heterocíclics
Síntesi orgànica
Heterocyclic compounds
Organic synthesis
Issue Date: 15-Jan-2021
Publisher: MDPI
Abstract: A synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3'-oxindole] framework present in a large number of oxindole alkaloids, with a cis H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an E-ethylidene substituent at C-20, is reported. The key steps of the synthesis are the generation of the tetracyclic spirooxindole ring system by stereoselective spirocyclization from a tryptophanol-derived oxazolopiperidone lactam, the removal of the hydroxymethyl group, and the stereoselective introduction of the E-ethylidene substituent by acetylation at the -position of the lactam carbonyl, followed by hydride reduction and elimination. Following this route, the 21-oxo derivative of the enantiomer of the alkaloid 7(S)-geissoschizol oxindole has been prepared.
Note: Reproducció del document publicat a:
It is part of: Molecules, 2021, vol. 26, p. 428-442
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ISSN: 1420-3049
Appears in Collections:Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)

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