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Australian Journal of Chemistry Australian Journal of Chemistry Society
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RESEARCH ARTICLE

Synthesis of Helical Molecules Based on 5,6,6a,7,8,12b-Hexahydrobenzo[c]phenanthrene-5,8-dione

J Cheung, LD Field, F Regaglia and S Sternhell

Australian Journal of Chemistry 48(10) 1707 - 1725
Published: 1995

Abstract

Synthetic routes based on Newman's1-7 synthesis of a number of polycyclic aromatic hydrocarbons were modified and developed to give a convenient preparation (Scheme 1) of 11 helical molecules formally based on hexalindione (1). In contrast to Newman's work determined the stereochemistry at C6a-C12b in (1a-k) and in some cases, were able to control it. We also investigated the competitive formation of six- and seven- membered rings in the reaction yielding the hexacyclic derivatives (1d, e). In addition, we report an unusual fragmentation (Scheme 2) leading to the unexpected by-product 4-methoxyacetophenone (16) in the synthesis of (1h).

https://doi.org/10.1071/CH9951707

© CSIRO 1995

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