| Naturally occurring indole-N-glycosides, such as Neosidomycin ( 1) and SF-2140 (2), have been shown to exhibit antibiotic activity. Many traditional methods for the synthesis of indole-N-glycosides have been investigated by other groups. Our approach to indole-N-glycosides involves the key inverse electron demand Diels-Alder cycloaddition reaction, which proceeds via an ortho-thiono-imino-quinone intermediate 85. When chlorine was present at C-5 of the ortho-thiono-imino-quinone 129, the cycloaddition reaction yield improved. |
