Issue 12, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
25 jul 2017
Accepted
29 ago 2017
First published
31 ago 2017

Org. Chem. Front., 2017,4, 2412-2416

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, 4, 2412 DOI: 10.1039/C7QO00633K

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