CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 107-121
DOI: 10.1055/s-0037-1610377
short review
Copyright with the author

Syntheses of Cyclomarins – Interesting Marine Natural Products with Distinct Mode of Action towards Malaria and Tuberculosis

Alexander Kiefer
,
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Publikationsverlauf

Received: 02. Oktober 2018

Accepted: 12. Oktober 2018

Publikationsdatum:
07. November 2018 (online)


Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

The cyclomarins are cyclic heptapeptides from marine streptomycetes containing four rather unusual amino acids. Interestingly, the cyclomarins address two completely different targets: ClpC1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Aase of Plasmodium falciparum. Therefore, the cyclomarins are interesting lead structures for the development of drugs targeting tuberculosis and malaria. As a result, several synthetic protocols towards the synthesis of these unusual building blocks as well as the natural products themselves have been developed, which will be discussed in this review.

1 Introduction

2 Synthesis of the Building Blocks

3 Total Synthesis of Cyclomarin C by Yao and Co-workers

4 Total Synthesis of Cyclomarin A and C by Barbie and Kazmaier

5 Conclusion