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Type: Artigo de periódico
Title: An Efficient Total Synthesis Of A Synthetic Equivalent Of The Prelog-djerassi Lactonic Acid
Author: Pilli R.A.
De Andrade C.K.Z.
Souto C.R.O.
Abstract: (3R, 5S, 6S, 1'S)- Tetrahydro- 6- (1'- methyl-2'-tert-butyldimethyl-silyloxyethyl)-3,5-dimethyl-2H-pyran-2-one (2a), a known precursor of the Prelog-Djerassi lactonic acid, has been prepared in 5 steps and 37% overall yield from (S)-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (3c). The key steps involved an aldol condensation of the boron enolate of (R)-N-propionyl-4-benzyl-2-oxazolidinone (4) and aldehyde 3c and an intramolecular alkylation of the potassium enolate of O-propionyl tosylate 6f.
Rights: aberto
Identifier DOI: 
Date Issue: 1996
Appears in Collections:Unicamp - Artigos e Outros Documentos

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