
TY  - JOUR
A1  - Cheung, J 
A1  - Field, LD 
A1  - Regaglia, F 
A1  - Sternhell, S 
T1  - Synthesis of Helical Molecules Based on 5,6,6a,7,8,12b-Hexahydrobenzo[c]phenanthrene-5,8-dione
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1995
VL  - 48
IS  - 10
SP  - 1707
EP  - 1725
KW  - 
UR  - https://doi.org/10.1071/CH9951707 
N2  - 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). 
ER  -

