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

Benjamin Laroche 1 Bastien Nay 1, 2, *
* Corresponding author
1 MCAM - Molécules de Communication et Adaptation des Micro-organismes (MCAM)
2 DCSO - Laboratoire de synthèse organique
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.
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Journal articles
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https://hal-polytechnique.archives-ouvertes.fr/hal-02093702
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Submitted on : Tuesday, April 9, 2019 - 10:42:28 AM
Last modification on : Friday, April 12, 2019 - 1:31:50 AM

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Benjamin Laroche, Bastien Nay. Harnessing the potential diversity of resinic diterpenes through visible light-induced sensitized oxygenation coupled to Kornblum–DeLaMare and Hock reactions. Organic Chemistry Frontiers, Royal Society of Chemistry, 2017, 4 (12), pp.2412-2416. ⟨10.1039/c7qo00633k⟩. ⟨hal-02093702⟩

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