4420-11-5Relevant articles and documents
Birch Reduction of Arenes as an Easy Entry to γ-Spirolactones
Krüger, Tobias,Bramborg, Andrea,Kelling, Alexandra,Sperlich, Eric,Linker, Torsten
, p. 6383 - 6391 (2021/11/18)
A convenient method for the synthesis of γ-spirolactones in only 2–3 steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of ethylene oxide affords hydroxy acids, which undergo direct lactonization during work-up. Suitable precursors are methyl-substituted benzoic acids, naphthoic, and dicarboxylic acids. Subsequent hydrogenation proceeds smoothly with Pd/C as catalyst and saturated γ-spirolactones are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation with Raney nickel or Wilkinson's catalyst to obtain products with 1 double bond. Overall, more than 30 new γ-spirolactones have been synthesized in analytically pure form.
SULFUR COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE
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Page/Page column 132, (2010/02/14)
The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
Titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides: A new method for the synthesis of γ-butanolides
Maslak, Veselin,Matovi?, Radomir,Sai?i?, Radomir N.
, p. 5411 - 5413 (2007/10/03)
A new method for the synthesis of γ-butanolides is described. The titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides, followed by acidic work-up, affords the corresponding butyrolactones in 44-83% yield.