| Autor: |
Mary Sexton, William P. Malachowski, Glenn P. A. Yap, Diana Rachii, Greg Feldman, Andrew T. Krasley, Zhilin Chen, My Anh Tran, Kalyn Wiley, Alexandra Matei, Samantha Petersen, Sabrina Tran Tien |
| Jazyk: |
angličtina |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
J Org Chem |
| Popis: |
Novel phenanthridinone analogs with an all-carbon quaternary stereocenter have been enantioselectively synthesized using the Birch-Heck sequence. Flat phenanthridinone structures have extensive bioactivity, but consequently also suffer from poor therapeutic selectivity. The addition of a quaternary center to the phenanthridinone skeleton has the potential to generate more complex analogs with improved selectivity. Unfortunately, no general synthetic pathway to such derivatives exists. Herein we report a four-step process that transforms inexpensive benzoic acid into twenty-two different quaternary carbon containing phenanthridinone analogs with a variety of substituents on all three rings: alkyl groups at the quaternary center; methyl, methoxymethyl or para-methoxybenzyl on the amide nitrogen; and halogen and methyl substituents on the aryl ring. Good to very good enantioselectivity was demonstrated in the key intramolecular desymmetrizing Mizoroki-Heck reaction. Transformations of the Heck reaction products into molecules with potentially greater therapeutic relevance were also accomplished. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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