Synthesis of Fluvirucins and Their Aglycons, the Fluvirucinins

Mercedes Amat; Núria Llor; Guillaume Guignard; Joan Bosch

doi:10.1055/s-0035-1561469

Synthesis, Table of Contents

Synthesis 2016; 48(17): 2705-2720
DOI: 10.1055/s-0035-1561469

short review

Synthesis of Fluvirucins and Their Aglycons, the Fluvirucinins

Mercedes Amat*

Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII 27-31, 08028 Barcelona, Spain Email: amat@ub.edu Email: joanbosch@ub.edu

,

Núria Llor

Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII 27-31, 08028 Barcelona, Spain Email: amat@ub.edu Email: joanbosch@ub.edu

,

Guillaume Guignard

Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII 27-31, 08028 Barcelona, Spain Email: amat@ub.edu Email: joanbosch@ub.edu

,

Joan Bosch*

Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII 27-31, 08028 Barcelona, Spain Email: amat@ub.edu Email: joanbosch@ub.edu

› Author Affiliations

Abstract

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Abstract

Fluvirucins are bioactive macrolactam glycosides isolated from actinomycetes. This review gives an overview of this family of natural products, covering isolation, biological activities, biosynthesis, and total synthesis. The synthesis of fluvirucins and their aglycons, the fluvirucinins, is presented, paying special attention to the synthetic strategy and stereochemical aspects.

1 Introduction

2 Isolation, Biological Activity, and Biosynthesis

3 Synthetic Approaches

3.1 Closure of the 14-Membered Ring by Ring-Closing Metathesis

3.2 Closure of the 14-Membered Ring by Macrolactamization

3.3 Construction of the 14-Membered Ring by Aza-Claisen Ring Expansion

4 Conclusion

Key words

macrolactams - synthetic strategy - ring-closing metathesis - macrolactamization - aza-Claisen rearrangement - stereoselectivity

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References

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