Rapid construction of the ABD tricyclic skeleton in meliacarpinin B from carvone enabled by an INOC strategy

Dong, Chang‐Ming; Qiao, Tianjiao; Xie, Yi; Zhang, Xiao; Ao, Junli; Liang, Guangxin

doi:10.1039/d0qo00576b

Cited by 2 publications

(1 citation statement)

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“…Fused isoxazoles or isoxazolines obtained by the INOC reaction may also serve as synthetically important intermediates for many biologically active compounds. Such compounds, including the HBV inhibitor entecavir [19,20], the antibiotic branimycin [21], the antiviral (+)-Brefeldin A [22], tricyclic isoxazoles combining serotonin (5-HT) reuptake inhibition with α 2 -adrenoceptor blocking activity [23] and the alkaloids meliacarpinin B [24] and Palhinine A [25], have been synthesized by employing INOC as a key step.…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis of Pyrazolo[4′,3′:5,6]pyrano[4,3-c][1,2]oxazoles via Intramolecular Nitrile Oxide Cycloaddition

et al. 2021

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A simple and efficient synthetic route to the novel 3a,4-dihydro-3H,7H- and 4H,7H-pyrazolo[4′,3′:5,6]pyrano[4,3-c][1,2]oxazole ring systems from 3-(prop-2-en-1-yloxy)- or 3-(prop-2-yn-1-yloxy)-1H-pyrazole-4-carbaldehyde oximes has been developed by employing the intramolecular nitrile oxide cycloaddition (INOC) reaction as the key step. The configuration of intermediate aldoximes was unambiguously determined using NOESY experimental data and comparison of the magnitudes of 1JCH coupling constants of the iminyl moiety, which were greater by approximately 13 Hz for the predominant syn isomer. The structures of the obtained heterocyclic products were confirmed by detailed 1H, 13C and 15N NMR spectroscopic experiments and HRMS measurements.

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