Convergent synthesis of Carpatamide-A: Cytotoxic arylamine derivative from marine derived Streptomyces sp.

Abstract

First total synthesis of carpatamide-A 7a, cytotoxic arylamine derivative isolated from marine derived Streptomyces sp., was achieved in twelve steps with overall yield of 24% with seven longest linear steps. In the penultimate step, dienoic acid 13 and an amino-phenylpropionic acid methyl ester core 21 were coupled to synthesize methylated derivativative of carpatamide-A 22 followed by demethylation of the intermediate with BBr₃ to accomplish carpatamide-A 7a. Both precursors 13 and 21 were synthesized from readily available starting materials i.e. isovaleraldehyde 8 and 2, 4-dihydroxy benzaldehyde 14.

Keywords:

• Convergent synthesis
• arylamine
• Carpatamide-A
• isovaleraldehyde
• Horner-Wadsworths-Emmons reaction

Acknowledgements

The authors wish to express their thanks to NIPER, SAS Nagar, Mohali, Punjab for providing necessary facilities to carry out this research work. The authors would also thank to Ministry of Chemical and Fertilizers, Govt. of India for NIPER Research fellowship Scheme.