The Synthesis of (±)‐Oxyisocyclointegrin. Issue 7 (25th January 2019)

• Record Type: Journal Article
• Authors: Smith, Robert J.; Bower, Rebekah L.; Ferguson, Scott A.; Rosengren, Rhonda J.; Cook, Greg M.; Hawkins, Bill C.
• Is Part Of: European journal of organic chemistry. Issue 7(2019)
• Page Start: 1571
• Page End: 1573
• Publication Date: 2019-01-25
• Subjects: Flavone -- Natural products -- Total synthesis -- Oxepine -- Antibacterial; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801751
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The total synthesis of oxyisocyclointegrin is described. The key steps in the synthesis included a Tsuji–Trost allyl migration to exclusively afford the corresponding monoallylated 1, 3‐diketone and a photochemical initiated oxidative cyclization to forge the oxepine core. Abstract : The total synthesis of the oxepine‐fused flavone natural product oxyisocyclointegrin is described. The synthesis was achieved in 7 steps and an overall yield of 15 %, oxyisocyclointegrin was found to possess moderate antibacterial activity and modest cytotoxicity.