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Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3‐Indandione to Fenestrindan
Author(s) -
Kuck Dietmar
Publication year - 1994
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.19941270218
Subject(s) - chemistry , diol , combinatorial chemistry , lewis acids and bases , stereochemistry , organic chemistry , catalysis
The synthesis and spectroscopic characterization of several benzoanellated [5.5.5]‐, [5.5.5.6]‐, and [5.5.5.5]fenestranes, including the parent difuso ‐centrotriindan 7 , the parent tetrafuso ‐centrotetraindan 8 (“fenestrindan”) as well as the tribenzo[5.5.5.6]‐ and tribenzo[5.5.5.5]fenestranes 27 and 35 , are described and discussed in full experimental detail. The highly efficient twofold cyclodehydration of 2,2‐dibenzyl‐1,3‐indandiol 15 and the related spiro‐condensed 1,3‐indandiols 23 and 29 is the keystep of the synthetic strategy. The new synthetic variant involving the one‐pot cyclodehydration/deketalization of the dispiro‐ketal diol 29 is particularly convenient. In the case of 7 , an alternative Lewis acid‐catalyzed double cyclization has been developed. Stereochemical aspects of the 1,3‐indandiols and the key tribenzo[5.5.5.6]fenestranes 24 and 25 are discussed in detail.