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Synlett 1996; 1996(10): 949-965
DOI: 10.1055/s-1996-5632
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By Cyclodehydration to Centropolyindanes: Development of a Novel Class of Indane Hydrocarbons with Three-dimensional Molecular Frameworks Using a Classical Synthetic Tool

Dietmar Kuck*
  • *Fakultät für Chemie, Universität Bielefeld, Universitätsstraße 25, D-33615 Bielefeld, Germany
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Publication Date:
31 December 2000 (online)

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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 1,3-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. Benzoanellated 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”.

Cyclization - cyclopentaannulation - dehydration (cyclodehydration) - indane hydrocarbons - propellanes - triquinacenes - fenestranes - polyquinanes

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