Tiacumicin B: An Antibiotic of Prime Importance and a Natural Product with an Inspiring Complex Structure

Emmanuel Roulland

doi:10.1055/s-0037-1609933

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(21): 4189-4200
DOI: 10.1055/s-0037-1609933

short review

Tiacumicin B: An Antibiotic of Prime Importance and a Natural Product with an Inspiring Complex Structure

Emmanuel Roulland

C-TAC, UMR 8638 CNRS/Université Paris Descartes, Faculté de Pharmacie, 4, avenue de l’Observatoire, 75006, Paris, France eMail: emmanuel.roulland@parisdescartes.fr

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Abstract

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Abstract

This short review aims at decrypting and analyzing the various strategies used for the synthesis of tiacumicin B. Natural products synthesis is a way for organic chemists to express inventiveness, intellectual dexterity, and elegance in strategy of synthesis. Some molecular structures are more inspiring than others; and if like tiacumicin B, the architectural challenge meets high biological and medicinal interest, the molecule can then attract the attention of many groups of synthetic chemists.

1 Introduction

2 The Strategic Challenges of this Total Synthesis

3 Construction of the C1–C5 Region

4 Construction of the C14–C19 Region

5 Construction of the C5–C12 Region

6 Construction of the C12–C15 Diene Motif

7 Macrocyclization

8 Synthesis of the Rhamnosyl Donor

9 Synthesis of the Noviosyl Donor and Glycosylation

10 The Recurrent Problems Caused by Protective Groups

11 Conclusion

Key words

total synthesis - natural products - antibiotic - metathesis - palladium catalysis - glycosylation

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Referenzen

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