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Literature DB >> 28377636

Formal synthesis of Thienamycin.

Michał Pieczykolan¹, Bartłomiej Furman¹, Marek Chmielewski¹.

Abstract

A formal synthesis of Thienamycin from ethyl (E)-crotonate and a cyclic five-membered nitrone derived from 2-deoxy-d-ribose is described. The synthesis involves 1,3-dipolar cycloaddition, cleavage of the N-O bond in the adduct, and intramolecular N-acylation to afford a bicyclic carbapenam skeleton. Subsequent transformations of the five-membered ring substituents provide the title compound.

Entities: Chemical

Mesh：

Substances：

Year: 2017 PMID： 28377636 DOI： 10.1038/ja.2017.44

Source DB: PubMed Journal: J Antibiot (Tokyo) ISSN： 0021-8820 Impact factor: 2.649

5 in total

1. Novel synthesis of (+)-4-acetoxy-3-hydroxyethyl-2-azetidinone from carbohydrate. A formal total synthesis of (+)-thienamycin.

Authors: K Tatsuta; M Takahashi; N Tanaka; K Chikauchi
Journal: J Antibiot (Tokyo) Date: 2000-10 Impact factor: 2.649

2. 1,3-Dipolar cycloaddition of a cyclic nitrone derived from 2-deoxy-D-ribose to α,β-unsaturated lactones: An entry to carbapenem antibiotics.

Authors: Michał Pieczykolan; Olga Staszewska-Krajewska; Bartłomiej Furman; Marek Chmielewski
Journal: Carbohydr Res Date: 2016-07-14 Impact factor: 2.104

1 in total

1. Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy.

Authors: You-Chen Lin; Aubert Ribaucourt; Yasamin Moazami; Joshua G Pierce
Journal: J Am Chem Soc Date: 2020-05-12 Impact factor: 15.419

1 in total

Formal synthesis of Thienamycin.

1. Novel synthesis of (+)-4-acetoxy-3-hydroxyethyl-2-azetidinone from carbohydrate. A formal total synthesis of (+)-thienamycin.

2. 1,3-Dipolar cycloaddition of a cyclic nitrone derived from 2-deoxy-D-ribose to α,β-unsaturated lactones: An entry to carbapenem antibiotics.

3. Synthesis of (+)-obtusenyne.

4. Total synthesis of ezetimibe, a cholesterol absorption inhibitor.

5. Synthesis of Thienamycin methyl ester from 2-deoxy-D-ribose via Kinugasa reaction.

1. Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy.