TY - JOUR
T1 - Metathesis reactions for the synthesis of ring-fused carbazoles
AU - Pelly, Stephen C.
AU - Parkinson, Christopher J.
AU - Van Otterlo, Willem A L
AU - De Koning, Charles B.
PY - 2005/12/9
Y1 - 2005/12/9
N2 - 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.
AB - 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.
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U2 - 10.1021/jo051826s
DO - 10.1021/jo051826s
M3 - Article
AN - SCOPUS:28744447770
SN - 0022-3263
VL - 70
SP - 10474
EP - 10481
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 25
ER -