TY  - JOUR
AB  - 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.
DA  - 1994
DO  - 10.1002/cber.19941270218
KW  - Polycyclic compounds
KW  - Fenestranes
KW  - Centropolyindans
KW  - Polyquinanes
LA  - eng
IS  - 2
M2  - 409
PY  - 1994
SN  - 0009-2940
SP  - 409-425
T2  - Chemische Berichte
TI  - 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
UR  - https://nbn-resolving.org/urn:nbn:de:0070-pub-17742285
Y2  - 2024-11-24T20:20:53
ER  -