Enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a diastereoselective aldol/beta-elimination sequence: application to the C(15)-C(21) fragment of tedanolide C.
An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.
Barth
Roland
R
Department of Chemistry, The Scripps Research Institute, Scripps Florida, 130 Scripps Way, Jupiter, Florida 33458, USA.
Roush
William R
WR
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D002264:Carboxylic Acids; D007094:Imides; D007659:Ketones; D018942:Macrolides; C516408:tedanolide C
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