Synthetic study on tetrapetalones: stereoselective cyclization of N-acyliminium ion to construct substituted 1-benzazepines.
The synthesis of the tetracyclic core of complex antibiotic tetrapetalones has been achieved in three steps starting from the simple intermediate gamma-hydroxy amide, which can be accessed through a high-yielding six-step sequence. The successful synthesis relies on a novel strategy based on the N-acyliminium ion cyclization.
Li
Cheng
C
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China.
Li
Xinyu
X
Hong
Ran
R
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D001552:Benzazepines / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D001552:Benzazepines; D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; D016859:Lipoxygenase Inhibitors; C492598:tetrapetalone A