Issue 19, 2019

Late-stage C–H amination of abietane diterpenoids

Abstract

This study aims at highlighting the synthetic versatility of the rhodium-catalyzed C–H amination reactions using iodine(III) oxidants for the late-stage functionalization of natural products. Inter- and intramolecular nitrene insertions have been performed from various abietane diterpenoids, leading to the amination of the C-3, C-6, C-7, C-11 and C-15 positions. Ca. 20 aminated compounds have been isolated with yields of up to 86% and high levels of regio-, chemo- and stereoselectivities.

Graphical abstract: Late-stage C–H amination of abietane diterpenoids

Supplementary files

Article information

Article type
Paper
Submitted
01 ဖေ 2019
Accepted
14 မတ် 2019
First published
22 မတ် 2019

Org. Biomol. Chem., 2019,17, 4736-4746

Late-stage C–H amination of abietane diterpenoids

M. I. Lapuh, A. Dana, P. H. Di Chenna, B. Darses, F. J. Durán and P. Dauban, Org. Biomol. Chem., 2019, 17, 4736 DOI: 10.1039/C9OB00272C

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