Abstract
Efficient synthesis, besides other, of dibromide, diazide, diamine and diesters derived from (11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (3), a chiral bicyclic diol with C2 symmetry, was developed. Esterification of 3 with saturated and unsaturated carboxylic acids and acids chlorides leads to the corresponding normal-, olefinic- and acetylenic diesters in average yields of 81%. Also more efficient techniques for the preparation of starting diol 3 in higher yields as well as for a very simple separation of DCU from reactions carried out following DCC/DMAP mehod are described.
Highlights
Chiral dihydroethano- and ethenoanthracene derivatives are versatile organic molecules with C2 symmetry that have been used in synthetic and biological applications
We are interested in reactions that involve the use of C2 symmetry substrates as precursors for the synthesis of optically active molecules with potential biological activity
We have reported the physical characteristics of a series of new TADDOLs unsaturated esters 4a and the use of these in the synthesis of macrolides via cyclohydrostanation reactions.4b In this context, we considered its convenient to synthesize a series of derivatives of the chiral diol (11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12dimethanol (3) and to study some reactions of them
Summary
Chiral dihydroethano- and ethenoanthracene derivatives are versatile organic molecules with C2 symmetry that have been used in synthetic and biological applications. They have been used as chiral ligands in enantioselective reactions, attached to a metal as catalytically active species, and as chiral polymers precursors.[1,2] Derivatives of C2-symmetric dicarboxylic acids are of interest since they can often be prepared on a large scale from available starting materials. The numerous routes from L-tartaric acid ilustrate this point well.[3] At present, we are interested in reactions that involve the use of C2 symmetry substrates as precursors for the synthesis of optically active molecules with potential biological activity. We have reported the physical characteristics of a series of new TADDOLs unsaturated esters 4a and the use of these in the synthesis of macrolides via cyclohydrostanation reactions.4b In this context, we considered its convenient to synthesize a series of derivatives of the chiral diol (11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12dimethanol (3) and to study some reactions of them
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