Abstract
Enantioselective construction of the protected carbocycle moiety of the anti-HIV drug carbovir was achieved in 11 steps from ( S)-(−)-ethyl lactate. The two key steps are a Claisen [3+3] sigmatropic rearrangement of (3 S,4 E)-3-(4-methoxy-phenoxymethyl)-hex-4-enoic acid dimethylamide and next, a ruthenium-catalysed ring closure metathesis leading to (1 S,4 S)-4-(4-methoxy-phenoxymethyl)-cyclopent-2-enol.
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