Photochemical Synthesis of Phenanthridines: Exploring Fluoro and Protected Catechol Substitution. Issue 18 (10th May 2013)

• Record Type: Journal Article
• Authors: Linsenmeier, Anna M.; Williams, Craig M.; Bräse, Stefan
• Is Part Of: European journal of organic chemistry. Issue 18(2013)
• Page Start: 3847
• Page End: 3856
• Publication Date: 2013-05-10
• Subjects: Natural products -- Fused heterocycles -- Photolysis -- Cyclization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300218
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Substituted phenanthridines, such as the natural product trispheridine, have been accessed by the practical photochemical cyclization of N ‐benzylanilines. Functionalities, with a focus on fluoro substituents and protected catechols, are well tolerated on both the A and C rings. The phenanthridines were accessed in good to very good yields (up to 95 %) from iodinated substrates, whereas brominated substrates performed poorly in comparison (0–48 %). Abstract : Substituted phenanthridines, such as the natural product trispheridine, can be accessed by the practical photochemical cyclization of N ‐benzylanilines, with functionalities tolerated on both the A and C rings. The phenanthridines are accessible in good to very good yields (up to 95 %) from iodinated substrates, whereas brominated substrates perform poorly in comparison (0–48 %).