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Total Synthesis of Incarnatapeptins A and B |
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| Authors: | Feipeng Han Jie Li Shupeng Li Zhuo Wang Dr. Yian Guo Prof. Dr. Tao Ye |
| Affiliation: | 1. State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen, 518055 China These authors contributed equally to this work. Contribution: Data curation (equal), Formal analysis (equal), Investigation (equal), Methodology (equal), Validation (equal);2. State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen, 518055 China Contribution: Conceptualization (supporting), Investigation (supporting), Project administration (supporting), Resources (supporting), Supervision (supporting), Writing - review & editing (supporting);3. Southern University of Science and Technology, Shenzhen, 518055 China Contribution: Data curation (supporting), Formal analysis (supporting);4. State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen, 518055 China |
| Abstract: | The first total synthesis of incarnatapeptins A and B, two novel marine natural products, was accomplished from readily available (S)-1-benzyloxycarbonylhexahydropyridazine-3-carboxylic acid. This route, whose longest linear sequence was 12 steps, provided the incarnatapeptins A and B in yields of 26.5 % and 19.7 %, respectively, and enabled the structure and stereochemistry of both natural products to be unambiguously confirmed. Highlights of our synthesis include the photoredox-mediated decarboxylative 1,4-addition reaction and a novel and practical N-acylation paradigm promoted by silver carbonate. The unusual facile atropisomerism of some linear peptidic intermediates was also observed by TLC analysis in the course of this work. |
| Keywords: | atropisomerism piperazic acid photocatalysis silver carbonate total synthesis |