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

Benjamin Laroche; Bastien Nay

doi:10.1039/c7qo00633k

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

Benjamin Laroche
, Bastien Nay

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	2412-2416
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	4
Issue number	12
DOIs	https://doi.org/10.1039/c7qo00633k
Publication status	Published - 1 Dec 2017

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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.",

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N2 - 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.

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

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