7-Oxabicyclo[4.1.0]heptane,1-methyl-4-(1-methylethenyl)-, (1S,4R,6R)-

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CAS: 6909-30-4
MF: C10H16O
MW: 152.23344
Synonyms: 7-Oxabicyclo[4.1.0]heptane,1-methyl-4-(1-methylethenyl)-, (1S,4R,6R)-

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Jin Qu

Nankai University
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Feng Wang

University of Science and Technology of China
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George Majetich

University of Georgia
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Phil S. Baran

The Scripps Research Institute
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David J. Cole-Hamilton

University of St. Andrews
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Paul Evans

University College Dublin
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Co-reporter: Kimberly Geoghegan, Paul Evans
pp: 1431-1433
Publication Date(Web):19 February 2014
DOI: 10.1016/j.tetlet.2014.01.039
(+)-Perillyl alcohol (1) has been synthesised in four steps and 39% overall yield from commercially available limonene oxide (4). The sequence features, as its key step, a palladium(0)-mediated transformation of a secondary allylic acetate (6) into its primary isomer (7). An application of (+)-perillyl alcohol (1) in a formal synthesis of naturally occurring (−)-mesembrine (2) and (−)-mesembranol was demonstrated.Image for unlabelled figure

Kellie L. Tuck

Monash University
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