Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5215833 | Tetrahedron | 2014 | 7 Pages |
Abstract
The first total synthesis of racemic scorzocreticin and its pure enantiomers is described from readily available 3,5-dihydroxybenzoic acid. The key steps include Wittig olefination, asymmetric Me-CBS (Corey-Bakshi-Shibata) oxazaborolidine reduction, and improved Pd-catalyzed intramolecular lactonization reactions. Both the (S)-natural and (R)-unnatural enantiomers of scorzocreticin have been synthesized in excellent enantioselectivities (>99% and 99% ee, respectively). In addition, 1,10-phenanthroline, a bidentate N-ligand was employed in palladium-catalyzed intramolecular carbonylation/lactonization reaction for the construction of 3,4-dihydroisocoumarin ring.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
B.T.V. Srinivas, Amarnath R. Maadhur, Sreedhar Bojja,