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

Lucia Pinčeková; Eva Jančiová; Dušan Berkeš; Róbert Gyepes; Andrej Kolarovič; Oľga Caletková

doi:10.3390/molecules28052177

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

Molecules. 2023 Feb 26;28(5):2177. doi: 10.3390/molecules28052177.

Authors

Lucia Pinčeková¹, Eva Jančiová¹, Dušan Berkeš¹, Róbert Gyepes², Andrej Kolarovič³, Oľga Caletková¹

Affiliations

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.

Keywords: Maillard reaction; alkaloid; crystallization-induced diastereomer transformation; diketopiperazine; glutamine; hydroxy amino acid; pyrrole.

Abstract

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