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The ester enolate claisen rearrangement. Total synthesis of (±)-ethisolide

✍ Scribed by Steven D. Burke; Gregory J. Pacofsky


Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
299 KB
Volume
27
Category
Article
ISSN
0040-4039

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An enantioselective route to the C(1) -C(6) erythronolide unit 10 is described, involving the dioxanone-to-dihydropyran enolate Claisen rearrangement (7 + 8), regio-and stereoselective hydroboration to give 9a, and reductive fragmentation of the heterocyclic template (9c + 10). The stereocontrolled