PUB - Publikationen an der Universität Bielefeld

Cyclodehydration of suitably 2-benzyl-substituted indan-1-ols and indan-1-ones and related compounds is a key synthetic tool for the highly efficient construction of three-dimensional carbocyclic frameworks containing several centrically condensed indane units. Inspired by a fortuitous cyclodehydration observed as a side reaction, this investigation has been spanned from two-fold cyclodehydration of 19-indanediols to ''bicyclodehydration'' of 1-indanones and 1,3-indanediones and to some directed applications of cyclodehydration of C-s-diindanols, C-s-diindanones, and C-s-diindanolones with sterically preoriented phenyl groups. Benzo-anellated triquinacenes and fenestranes, in particular, have become directly accessible by two-fold cyclodehydration, the latter including all-cis- but also cis,cis,cis,trans-fenestrane stereoisomers. Notwithstanding some limits of the strategy, the broad applicability of two-fold pentaannulation by cyclodehydration has led to the development of an entire class of novel polycyclic hydrocarbons, the ''centropolyindanes''.