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A three step synthesis of (R)-(-)-baclofen is described. The key step is the orthoester Claisen rearrangement of enantiopure allylic alcohol (S,E)-(-)-1a, affording y,δ-unsaturated ester (S,E)-(+)-6 with high stereoselectivity. This latter derivative is converted into (R)-(-)-baclofen through a high yield one-pot reaction.
Racemic hydroxylactones 11a and 11b were converted through the key aldehyde intermediate 21 into the C 6 -C 4 acid 22, showing all the necessary functionalities for the subsequent transformation into verapamil 1. Baker's yeast reduction of racemic ketolactone 8 provided enantiomerically pure 11a, close to the diastereoisomer 11b possessing 0.14 ee. The unusual chemical behaviour observed...
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