Formal radical cyclization onto benzene rings: a general method and its use in the synthesis of ent-nocardione A.
An indirect method is described for effecting radical cyclization onto a benzene ring. Cross-conjugated dienones 6, which are readily prepared from phenols, undergo radical cyclization (6 --> 7 --> 8), and the products (8) are easily aromatized. The method has been applied to the synthesis of ent-nocardione A (21).
Clive
Derrick L J
DL
Chemistry Department, University of Alberta, Edmonton, Alberta, Canada T6G 2G2. derrick.clive@ualberta.ca
Fletcher
Stephen P
SP
Liu
Dazhan
D
D001554:Benzene / Q000737:chemistry*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis*
D005609:Free Radicals; D005663:Furans; D009285:Naphthoquinones; C410782:nocardione A; D001554:Benzene