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

被引：0

作者：

Pincekova, Lucia ^{[1
]}

Janciova, Eva ^{[1
]}

Berkes, Dusan ^{[1
]}

Gyepes, Robert ^{[2
]}

Kolarovic, Andrej ^{[3
]}

Caletkova, Ol'ga ^{[1
]}

机构：

[1] Slovak Univ Technol Bratislava, Inst Organ Chem Catalysis & Petrochemistry, Radlinskeho 9, Bratislava 81237, Slovakia

[2] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Hlavova 2030, Prague 12840, Czech Republic

[3] Trnava Univ, Fac Educ, Dept Chem, Priemyselna 4, Trnava 91843, Slovakia

来源：

MOLECULES | 2023年 / 28卷 / 05期

关键词：

pyrrole; alkaloid; Maillard reaction; crystallization-induced diastereomer transformation; glutamine; hydroxy amino acid; diketopiperazine; ALPHA-AMINO ACIDS; DERIVATIVES;

D O I：

10.3390/molecules28052177

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页数：15

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