110013-17-7Relevant articles and documents
Synthesis of Both Enantiomers of γ-Substituted α,β-Unsaturated γ-Lactones
Bloch, R.,Gilbert, L.
, p. 4603 - 4605 (1987)
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Concise enantiodivergent synthesis of (+)- and (-)-trans-quercus lactones
Suzuki, Katsufumi,Shoji, Muneo,Kobayashi, Eriko,Inomata, Kohei
, p. 2789 - 2792 (2001)
A concise enantiodivergent total synthesis of (+)- and (-)-quercus lactones from the known tricyclic lactone (+)-1 as a single chiral template was achieved using the diastereoselective nucleophilic addition of organometallic reagents as the key step.
Organocatalytic sequential α-aminoxylation and cis-Wittig olefination of aldehydes: Synthesis of enantiopure γ-butenolides
Devalankar, Dattatray A.,Chouthaiwale, Pandurang V.,Sudalai, Arumugam
experimental part, p. 240 - 244 (2012/06/04)
A short route to enantiopure γ-butenolides (up to 99% ee) has been developed from readily available starting materials. The strategy involves a sequential organocatalytic α-aminoxylation followed by cis-Wittig olefination of aldehydes. The utility of this protocol has been demonstrated in the asymmetric synthesis of trans-(+)-cognac lactone with high enantiomeric purity.
Organo-catalyzed enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones as intermediates for natural products
Chowdhury, Raghunath,Ghosh, Sunil K.
experimental part, p. 1895 - 1900 (2012/01/05)
The enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones has been achieved by an organo-catalyzed Michael addition of enolizable aldehydes onto a silylmethylene malonate followed by a silicon-facilitated Bayer-Villiger oxidation of the β-silyl aldehyde adducts as the key step. γ-Alkyl γ-butenolides were obtained from the β-silyl γ-alkyl γ-butyrolactones by Fleming-Tamao oxidation of the silyl group to a hydroxy group and subsequent elimination. These butenolides are the advanced intermediates of some natural products such as (+)-γ-caprolactone, (+)-methylenolactocine, and (-)-quercus lactone.
