Metathesis reactions for the synthesis of ring-fused carbazoles.
J Org Chem
; 70(25): 10474-81, 2005 Dec 09.
Article
in En
| MEDLINE
| ID: mdl-16323860
ABSTRACT
[reactions see text] 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, we 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 pi8 electrocyclization reaction.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Carbazoles
Language:
En
Journal:
J Org Chem
Year:
2005
Type:
Article