Tetrahedron

A FeCl 3-promoted highly atropodiastereoselective cascade reaction: Synthetic utility of radical cations in indolostilbene construction

K Ahmad, NF Thomas, MR Mukhtar, I Noorbatcha…

Index: Ahmad, Kartini; Thomas, Noel F.; Mukhtar, Mat Ropi; Noorbatcha, Ibrahim; Faizal Weber, Jean-Frederic; Nafiah, Mohd Azlan; Velu, Saraswati S.; Takeya, Koichi; Morita, Hiroshi; Lim, Chuan-Gee; Hadi, A. Hamid A.; Awang, Khalijah Tetrahedron, 2009 , vol. 65, # 7 p. 1504 - 1516

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Citation Number: 11

Abstract

The FeCl3-promoted oxidative cyclization/coupling of acetamidostilbenes possessing 3- methoxy, 4-methoxy and 3, 5-methoxy substitutions (21),(22) and (23) is described. Only 3, 5- substitution gave rise to novel indolostilbenes, each possessing two stereogenic axes (axially chiral but racemic dimers (39) and (40)). The 4-methoxy substituted acetamidostilbenes, by contrast, yielded the bisindoline dimer (36).

~2%

Detail

~47%

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