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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

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パキシリン・インドール・ディテルペンの簡潔なアプローチ

David T George1, Eric J Kuenstner1, Sergey V Pronin1

  • 1Department of Chemistry, University of California , Irvine, California 92697-2025, United States.

Journal of the American Chemical Society
|November 24, 2015
PubMed
まとめ

研究者はパキシリン・インドル・ディターペンの新合成経路を開発した. この効率的な方法は,複合ペンタサイクルのコアを構成し,エミンドールSBの合成を可能にします.

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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