Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone-Reference-Cited by-同舟云学术

Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone

Published:2023-02-26 Issue:5 Volume:28 Page:2177
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Pinčeková Lucia¹,Jančiová Eva¹,Berkeš Dušan¹^ORCID,Gyepes Róbert²^ORCID,Kolarovič Andrej³^ORCID,Caletková Oľga¹

Affiliation:

1. Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia

2. Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague, Czech Republic

3. Department of Chemistry, Faculty of Education, Trnava University, Priemyselná 4, 918 43 Trnava, Slovakia

Abstract

Total synthesis of the 2-formylpyrrole alkaloid hemerocallisamine I is presented, both in racemic and enantiopure form. Our synthetic strategy involves (2S,4S)-4-hydroxyglutamic acid lactone as the key intermediate. Starting from an achiral substrate, the target stereogenic centers were introduced by means of crystallization-induced diastereomer transformation (CIDT) in a highly stereoselective fashion. A Maillard-type condensation was crucial to constructing the desired pyrrolic scaffold.

Funder

Slovak Research and Development Agency

Scientific Grant Agency of the Slovak Republic

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

https://www.mdpi.com/1420-3049/28/5/2177/pdf

Reference46 articles.

1. (2023, January 31). Plants of the World Online (POWO). Available online: https://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:24324-1.

2. (2023, January 31). American Daylily Society. Available online: https://daylilydatabase.org/.

3. Analysis and Stability of Carotenoids in the Flowers of Daylily (Hemerocallis disticha) as Affected by Various Treatments;Tai;J. Agric. Food Chem.,2000

4. Progress of genus Hemerocallis in traditional uses, phytochemistry, and pharmacology;Li;J. Hortic. Sci. Biotechnol.,2022

5. Matraszek-Gawron, R., Chwil, M., Terlecka, P., and Skoczylas, M.M. (2019). Recent Studies on Anti-Depressant Bioactive Substances in Selected Species from the Genera Hemerocallis and Gladiolus: A Systematic Review. Pharmaceuticals, 12.