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Please use this identifier to cite or link to this item: http://hdl.handle.net/10204/2040

Title: Metathesis reactions for the synthesis of ring-fused carbazoles
Authors: Pelly, SC
Parkinson, CJ
Van Otterlo, WAL
De Koning, CB
Keywords: Metathesis reactions
Furostifoline synthesis
Tert butyl methyl
Organic chemistry
Issue Date: 9-Dec-2005
Publisher: American Chemical Society
Citation: Pelly, SC, et al. 2005. Metathesis reactions for the synthesis of ring-fused carbazoles. Journal of Organic Chemistry, vol. 70(25), pp 10474-10481
Abstract: The metathesis reaction is used as a key step for the synthesis of the indolo [2,3-a] carbazole core of rebeccamycin 13 and the sulfur analog of furostifoline 21. Using the same methodology for the attempted synthesis of furostifoline, the authors unexpectedly formed tert-butyl-2a-methyl-1,2,2a,10c-tetrahydro-6H-cyclobuta[c]furo[3,2-a]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 pi(8) electrocyclization reaction.
URI: http://hdl.handle.net/10204/2040
ISSN: 0022-3263
Appears in Collections:General science, engineering & technology
Discovery chemistry

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