Synthesis and CD spectroscopic study of chiral C2-symmetric (+)-2-oxaadamantane-4,8-dione.
The enantiomerically pure (-)-(1R,3S,4S,6R,8R)-4-bromo-3-methoxy-2-oxatricyclo[4.3.1.0(3,8)]decan-10-one 1 was transformed into a chiral C2-symmetric molecule (+)-(1R,3R,5R,7R)-2-oxatricyclo[3.3.1.1(3,7)]decane-4,8-dione (2-oxaadamantane-4,8-dione) 2 by a silver nitrate promoted molecular rearrangement/debromination reaction. The Cotton effect in the circular dichroism spectrum of the C2-symmetric (+)-2-oxaadamantane-4,8-dione was studied to prove the absolute configuration.
Zilinskas
Albinas
A
Department of Organic Chemistry, Vilnius University, Vilnius, Lithuania. albinas.zilinskas@chf.vu.lt
Stoncius
Sigitas
S
Butkus
Eugenius
E