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Enantioselective Synthesis of the 5–6–7 Carbocyclic Core of the Gagunin Diterpenoids

✍ Scribed by Shibuya, Grant M.; Enquist, John A.; Stoltz, Brian M.


Book ID
120513870
Publisher
American Chemical Society
Year
2013
Tongue
English
Weight
671 KB
Volume
15
Category
Article
ISSN
1523-7060

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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 ruthen