European Journal of Organic Chemistry p. 4472 - 4476 (2014)
Update date:2022-08-04
Topics: NMR spectroscopy Stereochemistry Total synthesis Enantioselective synthesis Diels-Alder Reaction Chiral Auxiliary
Lee, Jong Seok
Shin, Junho
Shin, Hee Jae
Lee, Hwa-Sun
Lee, Yeon-Ju
Lee, Hyi-Seung
Won, Hoshik
Gold(I)-catalyzed intramolecular 6-endo-dig cyclization of tert-butyl ynoates afforded α-pyrone cores of violapyrones. Moreover, this reaction was successfully applied to the stereospecific syntheses of (+)- and (-)-violapyrone C, which allowed the absolute configuration of natural (+)-violapyrone C to be assigned by comparison of the optical rotations. This first total synthesis, which proceeded in 22% yield over 10 steps from (S)-(-)-2-methylbutanol, features silver(I) oxide promoted monobenzylation of 1,4-butanediol, Wittig olefination, Claisen condensation, Corey-Fuchs reaction, and gold(I)-catalyzed α-pyrone synthesis. Copyright
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