Synthesis 2016; 48(17): 2705-2720
DOI: 10.1055/s-0035-1561469
short review
© Georg Thieme Verlag Stuttgart · New York

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
Further Information

Publication History

Received: 21 April 2016

Accepted after revision: 29 April 2016

Publication Date:
23 June 2016 (online)


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

 
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