First Total Synthesis of N‐(3‐Guanidinopropyl)‐2‐(4‐hydroxyphenyl)‐2‐oxoacetamide |
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| Authors: | Satish S. More Akula Raghunadh Ramanathan Shankar Navin B. Patel Dinesh S. Bhalerao Unniaran K. Syam Kumar |
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| Affiliation: | 1. Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy's Laboratories Ltd., Miyapur, Hyderabad 500049, India;2. Department of Chemistry, Veer Narmad South Gujarat University, Udhana‐Magdalla Road, Surat, India;3. Integrated Product Development, Innovation Plaza, Dr. Reddy's Laboratories Ltd., Bachupalli, Qutubullapur, R.R. Dist., 500072, Andhra Pradesh, India |
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| Abstract: | The first total synthesis of the α‐oxo amide‐based natural product, N‐(3‐guanidinopropyl)‐2‐(4‐hydroxyphenyl)‐2‐oxoacetamide ( 3 ), isolated from aqueous extracts of hydroid Campanularia sp., has been achieved. The α‐oxo amide 12 , prepared via the oxidative amidation of 1‐[4‐(benzyloxy)phenyl]‐2,2‐dibromoethanone ( 9a ) with 4‐{[(tert‐butyl)(dimethyl)silyl]oxy}butan‐1‐amine ( 10a ), has been used as the key intermediate in the total synthesis of 3 as HBr salt. On the way, an expeditious total synthesis of polyandrocarpamide C ( 2c ), isolated from marine ascidian Polyandrocarpa sp., was carried out in four steps. |
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| Keywords: | Ethanones, dibromo‐ Amides, α ‐oxo Oxidative amidation Total synthesis |
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