用于合成稠环咔唑的复分解反应。
Metathesis reactions for the synthesis of ring-fused carbazoles.
作者信息
Pelly Stephen C, Parkinson Christopher J, van Otterlo Willem A L, de Koning Charles B
机构信息
Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, P.O. Wits, 2050 South Africa.
出版信息
J Org Chem. 2005 Dec 9;70(25):10474-81. doi: 10.1021/jo051826s.
[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.
[反应：见正文] 复分解反应是合成瑞贝克霉素13的吲哚并[2,3-a]咔唑核心以及呋甾替林21的硫类似物的关键步骤。我们使用相同的方法尝试合成呋甾替林，意外地从不稳定的二烯叔丁基2-(2-异丙烯基-3-呋喃基)-3-乙烯基-1H-吲哚-1-羧酸酯25中形成了叔丁基-2a-甲基-1,2,2a,10c-四氢-6H-环丁烷[c]呋喃并[3,2-a]咔唑-6-羧酸酯26，推测是通过自发的π8电环化反应。
Zotero 插件