Abstract

The first total synthesis of carmabin A and dragomabin was achieved at 52.3 mg and 43.8 mg scale, respectively. The synthesis led to determination of the configuration of carmabin A and reassignment of the configuration of dragomabin at the stereogenic centre on the alkyne-bearing fragment.

Highlights

  • Secondary metabolites produced by marine microorganisms are a rich source of valuable pharmaceuticals ranging from antimalarial agents to anticancer agents [1,2,3,4]

  • Dragomabin may providestereochemical new leads for drug discovery. of we report the first total we thestereochemical first total synthesis of dragomabin with a A

  • With 7, 5, ent-5 in hand, we aimed at completing the total synthesis of carmabin A and

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Summary

Introduction

Secondary metabolites produced by marine microorganisms are a rich source of valuable pharmaceuticals ranging from antimalarial agents to anticancer agents [1,2,3,4]. Marine cyanobacteria are widely distributed throughout the world [5] and produce a large number of structurally complex secondary metabolites containing alkynyl groups [6]. Due to their intriguing biological activities, these compounds have attracted the attention of many synthetic chemists [7,8,9,10,11,12,13], including us [14]. Dragomabin, which has lost a propyl unit compared to carmabin A, showed antimalarial activity (6.0 μM) towards the W2 chloroquine-resistant malaria strain but very weak cytotoxicity to Vero cells

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