Despite centuries-long use of Cannabis in human culture and the now ubiquitous claims of its medicinal value, only a small handful of phytocannabinoids have been rigorously evaluated for pharmacological properties. While more than 100 distinct minor cannabinoids have been documented to date, a paucity of studies on their biological activities have been conducted due to a lack of routine access to sufficient quantities for testing. Herein, we report a strategy to prepare several structurally diverse minor cannabinoids deriving synthetically from readily available cannabidiol. Furthermore, we examined their ability to polarize activated microglia toward an antiinflammatory phenotype using LPS-stimulated BV2 microglial cells. The minor cannabinoids studied, especially cannabielsoin, dehydrocannabielsoin, cannabimovone, and 3′-epicannabimovone, inhibited the production of prototypical pro-inflammatory biomarkers. This study represents the beginning of a systematic mapping of the roles minor cannabinoids may play in the medicinal properties of cannabis used for the treatment of pain and inflammation.
Herein, we report
a study on the reactivity of three 1,3-diarylimidazolium-based
fluoride reagents, with a general formula of [IPrH][F(HF)
n
] (
n
= 0, 1, or 2), that tackle
the challenges of limited solubility, hygroscopicity, instability,
and laborious preparation procedures of nucleophilic fluoride reagents.
Fluorination of 4-
tert
-butylbenzyl bromide reveals
that trifluoride [IPrH][F(HF)
2
] is the most selective reagent.
Microwave-assisted activation coupled with the addition of sterically
hindered amine DIPEA or alkali metal fluorides increases the rate
of fluorination with [IPrH][F(HF)
2
], making it an excellent
reagent for the fluorination of various organic substrates. The scope
of substrates includes benzyl bromides, iodides, chlorides, aliphatic
halides, tosylates, mesylates, α-haloketones, a silyl chloride,
acyl and sulfuryl chlorides, and a nitroarene. The exceptional stability
of the air-stable and nonhygroscopic [IPrH][F(HF)
2
] reagent
is illustrated by its convenient synthesis and detailed experimental
regeneration protocol using hydrofluoric acid without organic solvents.
Heterogeneity of meroterpenoids arising from their dual biosynthetic origins is constantly provoking synthetic chemists to utilize their ingenuity and revise their retrosynthetic logic. By studying recent publications on meroterpenoid synthesis,tremendous advances in the field of synthetic organic chemistry can be witnessed. This feature article covers some of the most intriguing total syntheses and synthetic studies towards the meroterpenoid class of natural products from the last five years.
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