Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide

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Date
2007-06-19
Authors
O'Sullivan, Timothy P.
Zhang, Hongbin
Mander, Lewis N.
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Royal Society of Chemistry
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Abstract
In model studies towards the synthesis of harringtonolide, the construction of the tropone moiety via arene cyclopropanation was investigated. The installation of the lactone ring was accomplished by way of a Diels-Alder cycloaddition of various indenones and 𝛼-pyones. The incorporation of the key bridge methyl group and subsequent control of its stereochemistry is also outlined.
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Cyclopropanation , Diels-Alder cycloaddition , Diterpenoid , Harringtonolide , Lactone ring , Aromatic compounds , Bioactivity , Biosynthesis , Cyclopropanation reactions , Ketones , Lactones , Functional groups , Stereochemistry , Biomolecules
Citation
O'SULLIVAN, T. P., ZHANG, H. & MANDER, L. N. 2007. Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide. Organic & Biomolecular Chemistry, 5, 2627-2635. http://dx.doi.org/10.1039/B707467K
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© The Royal Society of Chemistry 2007