Total Synthesis of (±)-Herbertenolide by Stereospecific Formation of Vicinal Quaternary Centers in a Crystalline Ketone
- 28 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (4), 645-647
- https://doi.org/10.1021/ol0499250
Abstract
The sesquiterpene (±)-herbertenolide was synthesized in seven steps from commercial 2-bromo-4-methylanisole. In the key step, two adjacent stereogenic quaternary centers were controlled by a highly chemoselective and stereospecific photodecarbonylation reaction of crystalline methyl-trans-3-(2-methyl-5-methoxyphenyl)-1,3-dimethyl-2-oxocyclohexancarboxylate (3). An efficient generation of radical pairs and the stereochemical control exerted by the solid state suggest that this reaction may become a useful synthetic method.Keywords
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