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

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

Key words

natural products - cyclopeptides - cyclomarins - total synthesis - malaria - tuberculosis

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