The Pivotal Role of N‐O bonds in the Synthesis of Natural Products: A mini‐review

Abstract

This review focuses on the role of the nitrogen‐oxygen bond as a structural cornerstone for the construction of complex natural products. This bond may play several roles such as a functional protecting group or an activating group in carbonyl chemistry. Compounds containing a N‐O bond are generally prepared by cycloaddition of nitroso derivatives, nitrones or nitriles oxides. The first two reactions have been used in the synthesis of a N‐O bond containing natural product, pyrinodemin A, or for the synthesis of hydroxylated piperidine alkaloids after N‐O bond cleavage.

Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions

“…The five-membered N,Oring constitutes a central scaffold for natural compounds such as pyrinodemines. [6] In addition, isoxazolines are useful intermediates in organic synthesis. [1,7] For instance, reductive cleavage of the NÀ O bond can yield valuable products, such as 1,3-aminoalcohol or β-hydroxyketone.…”