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Enantioselective synthesis of the carbocyclic moiety of (−)-carbovir

✍ Scribed by Emmanuel Roulland; Claude Monneret; Jean-Claude Florent

Book ID
104253531
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
156 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 (3S,4E)-3-(4-methoxy-phenoxymethyl)-hex-4-enoic acid dimethylamide and next, a ruthenium-catalysed ring closure metathesis leading to (1S,4S)-4-(4methoxy-phenoxymethyl)-cyclopent-2-enol.

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