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Preparation of t-butyl 4-diethylphosphono-3-oxobutanethioate and use in the synthesis of (E)-4-alkenyl-3-oxoesters and macrolides

โœ Scribed by Steven V. Ley; Peter R. Woodward

Book ID
104227381
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
132 KB
Volume
28
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The preparation of t-butyi! 4-diethyZphosphono-3-oxobutanethioate (1) and Wadsworth-hnons reaction with aldehydes and ketones is reported. Some of the products of these reactions were converted to unsaturated 3-oxocolnacrolides or 3-oxodiolides by transesterification in the presence of copper-(I)-trifluoroacetate.

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Use of t-butyl 4-diethylphosphono-3-oxob
Use of t-butyl 4-diethylphosphono-3-oxobutanethioate for tetramic acid synthesis: Total synthesis of the plasmodial pigment fuligorubin A
โœ Steven V. Ley; Stephen C. Smith; Peter R. Woodward ๐Ÿ“‚ Article ๐Ÿ“… 1988 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 164 KB

A short, efficient synthesis of the yellow slime mould pigment fuligorubin A (I) has been achieved using coupling of t-butyl4-diethylphosphono-3-oxobutanethioate with deca-2,4,6,8-tetraenal and subsequent substitution with a glutamic acid derivative followed by Dieckmann cyclisation. The polyene ac