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Benzoanellated centropolyquinanes, 12 [1] trifuso ‐centrotetraindan – two syntheses of a new centropolyindan
Author(s) -
Kuck Dietmar,
Seifert Monika
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250624
Subject(s) - chemistry , steric effects , ketone , yield (engineering) , fragmentation (computing) , stereochemistry , medicinal chemistry , organic chemistry , materials science , computer science , metallurgy , operating system
Two independent syntheses of the new centrotetraindan 2 , a “ trifuso”, C s ‐symmetrical isomer of fenestrindan 1 , are described. The first approach is based on the “ endo ”‐phenyldiindanone 7 , which is converted into 2 by benzylation to ketone 8 and subsequent cyclodehydration with polyphoshoric acid. The second, more efficient approach is based on the diindan‐dione 17 , which is converted into ketol 19 in two steps, which, in turn, is subjected to a three‐step cyclodehydration‐reduction‐cyclodehydration sequence via 26 and 27 to give 2 in 8% overall yield. Some limits of the cyclodehydration of diindan alcohols and ketones are demonstrated with regard to effects of steric crowding and fragmentation of the carbon skeleton. The steric hindrance of “ endo ”‐phenyl‐substituted diindans is demonstrated in the case of ketone 26 .