Scalable synthesis of cladosporin |
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Authors: | Pronay Das Yash Mankad D. Srinivasa Reddy |
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Affiliation: | 1. Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India;2. Academy of Scientific and Innovative Research (AcSIR), New Delhi 110 025, India |
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Abstract: | Cladosporin, a secondary metabolite isolated from fungal sources like Cladosporium cladosporioides and Aspergillus flavus was found to exhibit selective nano-molar activity against malarial parasite Plasmodium falciparum by inhibiting parasitic protein biosynthesis. In addition, this natural product has a broad range of bioactivities including, antiparasitic, antifungal, antibacterial as well as plant growth inhibition. However, it has limited availability from the natural sources for further development. Herein, we report a modified and improved synthetic route which led us to produce this potent natural product in a gram scale. Conversion of the undesired diastereomer to desired one via Mitsunobu inversion of secondary alcohol and carbon monoxide insertion reaction towards the construction of isocoumarin unit are the key features of the present synthesis. |
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Keywords: | Cladosporin Total synthesis Anti-malarials Mitsunobu |
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