Metathesis reactions for the synthesis of ring-fused carbazoles

Stephen C. Pelly, Christopher J. Parkinson, Willem A L Van Otterlo, Charles B. De Koning

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76 Citations (Scopus)

Abstract

The metathesis reaction is used as a key step for the synthesis of the indolo[2,3-α]carbazole core of rebeccamycin 13 and the sulfur analog of furostifoline 21. Using the same methodology for the attempted synthesis of furostifoline, we unexpectedly formed tert-butyl-2a-methyl-1,2,2a,10c- tetrahydro-6H-cyclobuta[c]furo[3,2-α]carbazole-6-carboxylate 26 from the unstable diene, tert-butyl 2-(2-isopropenyl-3-furyl)-3-vinyl-1H-indole-1- carboxylate 25, presumably via a spontaneous π8 electrocyclization reaction.

Original languageEnglish
Pages (from-to)10474-10481
Number of pages8
JournalJournal of Organic Chemistry
Volume70
Issue number25
DOIs
Publication statusPublished - 09 Dec 2005

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