112185-24-7Relevant academic research and scientific papers
PREPARATION OF t-BUTYL 4-DIETHYLPHOSPHONO-3-OXOBUTANETHIOATE AND USE IN THE SYNTHESIS OF (E)-4-ALKENYL-3-OXOESTERS AND MACROLIDES
Ley, Steven V.,Woodward, Peter R.
, p. 345 - 346 (1987)
The preparation of t-butyl 4-diethylphosphono-3-oxobutanethioate (1) and Wadsworth- Emmons reaction with aldehydes and ketones is reported.Some of the products of these reactions were converted to unsaturated 3-oxomacrolides or 3-oxodiolides by transester
Further Reactions of t-Butyl 3-Oxobutanthioate and t-Butyl 4-Diethylphosphono-3-oxobutanthioate: Carbonyl Coupling Reactions, Amination, Use in The Preparation of 3-Acyltetramic Acids and Application to The Total Synthesis of Fuligorubin A.
Ley, Steven V.,Smith, Stephen C.,Woodward, Peter R.
, p. 1145 - 1174 (2007/10/02)
Key words: Acyltetramic acid; Phosphonate; Wadsworth-Emmons; Dieckmann cyclisation; Fuligorubin A. Abstract: The use of t-butyl-3-oxobutanthioate (1) and t-butyl 4-diethylphosphono-3-oxobuthanthioate (2) for the preparation of homologated derivatives suitable for amination in the presence of silver(I) trifluoroacetate to afford the corresponding β-ketoamides is discussed.In particular Wadsworth-Emmons coupling reactions of (2) with various carbonyl compounds gave good yields of E-substituted products.Many of the β-ketoamides were shown to be suitable precursors for 3-acyltetramic acids using a Dieckman cyclisation with tetra-n-butyl ammonium fluoride as the cyclising base.These new reactions were applied to the total synthesis of the polyene 3-acyltetramic acid fuligorubin A.
