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Harnessing the potential diversity of resinic diterpenes through visible light-induced sensitized oxygenation coupled to Kornblum–DeLaMare and Hock reactions

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Abstract

A biomimetic procedure for the late-stage functionalization of various resinic acids is reported, implementing photooxygenation by singlet oxygen, using visible light and meso-tetraphenylporphyrin, combined to the Kornblum–DeLaMare reaction or the Hock rearrangement. In addition to giving access to several natural and unnatural diterpenes by the simplest manner, these transformations furnish biosynthetic clues expandable to other natural product families.

Graphical abstract: Harnessing the potential diversity of resinic diterpenes through visible light-induced sensitized oxygenation coupled to Kornblum–DeLaMare and Hock reactions

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Publication details

The article was received on 25 Jul 2017, accepted on 29 Aug 2017 and first published on 31 Aug 2017


Article type: Research Article
DOI: 10.1039/C7QO00633K
Citation: Org. Chem. Front., 2017, Advance Article
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    Harnessing the potential diversity of resinic diterpenes through visible light-induced sensitized oxygenation coupled to Kornblum–DeLaMare and Hock reactions

    B. Laroche and B. Nay, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00633K

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