N-cyanoindoles and n-cyanoindole-4,7-diones: Construction of a bc ring synthon for the kinamycins

✍ Scribed by Gary I. Dmitrienko; Kent E. Nielsen; Christopher Steingart; Sai Ming Ngai; Jennifer M. Willson; Gamini Weeratunga

• Book ID: 104228700
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 298 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97443-4

✦ Synopsis

available by reaction of N-sodioindoles with phenyl cyanate, are substantially less reactive than N-acylindoles under electrophilic bromination conditions but readily yield sklechain brominated products under free radical conditions. Ceric ammonium nitrate oxidation of Ncyano-4,7dimethoxy-2.3~disubstituted indoles yields the carresponding N-cyanoindole-4,7diones which are potentially sy-nthons for construction of kinamycins, 1. The kinamycin antibioticsl, 1, incorporate an unusual N-cyanoindoloquinone substructure, 2, which is unique among natural products and appears to have no counterpart among synthetic indole derivatives 2. Elegant applications of DC, 15N and %I labelling and 2D NMR techniques have recently led to the elucidation of much of the biosynthetic route to these compounds.~.7 No reports of the chemical synthesis of either the kinamycins, 1, or simple analogs incorpoming the part strucnue 2, have appeaml in the literature.