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Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A 9 , and (±)-Fasamycin A: Structure-Activity Relationship Studies against Drug-Resistant Bacteria.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2018 Jun 15; Vol. 83 (12), pp. 6508-6523. Date of Electronic Publication: 2018 May 30. - Publication Year :
- 2018
-
Abstract
- Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (±)-naphthacemycin A <subscript>9</subscript> , and (±)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.
- Subjects :
- Structure-Activity Relationship
Biphenyl Compounds chemical synthesis
Biphenyl Compounds pharmacology
Drug Resistance, Microbial drug effects
Gram-Positive Bacteria drug effects
Naphthacenes chemical synthesis
Naphthacenes pharmacology
Polycyclic Aromatic Hydrocarbons chemical synthesis
Polycyclic Aromatic Hydrocarbons pharmacology
Polycyclic Compounds chemical synthesis
Polycyclic Compounds pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 83
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 29785848
- Full Text :
- https://doi.org/10.1021/acs.joc.8b00802