- Soft-enolization Baker-Venkataraman Rearrangement Enabled Total Synthesis of Dirchromones and Related 2-Substituted Chromones
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A seven-step total synthesis of the original scaffold of cytotoxic dirchromones involving an unprecedented soft-enolization Baker-Venkataraman rearrangement was designed. The methodology enabled access to naturally occurring dirchromone 1 (21% overall yield) at gram-scale, which was screened for cytotoxicity against 13 cancer cell lines. The scope of the soft-enolization Baker-Venkataraman rearrangement encompasses diversely substituted dirchromones, including flavonoids, 2-styrylchromones, and 2-phenylethylchromones.
- St-Gelais, Alexis,Alsarraf, Jér?me,Legault, Jean,Gauthier, Charles,Pichette, André
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supporting information
p. 7424 - 7428
(2019/01/03)
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- Fluoride ion-catalyzed conjugate addition for easy synthesis of 3-sulfanylpropionic acid from thiol and α,β-unsaturated carboxylic acid
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3-Sulfanylpropionic acids are obtained in excellent yields by proceeding through a simple, mild, and efficient procedure utilizing tetrabutylammonium fluoride (TBAF) as catalyst.
- Gao, Shijay,Tseng, Chi,Tsai, Cheng Hsuan,Yao, Ching-Fa
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p. 1955 - 1961
(2008/09/17)
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- An improved and green preparation of 3-(alkylthio)propionic acids
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An efficient, facile microwave-assisted synthesis has been developed for the preparation of unsymmetrical sulfide derivatives from 3-mercaptopropionic acid and a wide variety of alkyl, allyl or aryl chlorides or bromides. The synthesis performed in ethanol at 80 or 120 °C using sodium hydroxide as a base, selectively without an offensive smell, generates 3-(alkylthio)propionic acids in good yields. Effects of reaction components, temperature, and the heating technique on the formation of the product and side-products were studied.
- Vaismaa, Matti J. P.,Yliniemel?, Sanna M.,Lajunen, Marja K.
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p. 1317 - 1323
(2008/10/09)
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