The pinene scaffold: its occurrence, chemistry, synthetic utility, and pharmacological importance

Abstract

This review provides insight into the utility of pinene in the synthetic building block and as reagent in asymmetric synthesis.

Highly Efficient Cationic Polymerization of β-Pinene, a Bio-Based, Renewable Olefin, with TiCl4 Catalyst from Cryogenic to Energy-Saving Room Temperature Conditions

“…(see e.g., Refs. [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ] and references therein). Beyond doubt, β-pinene, which is the most abundant commercial terpene and is obtained from turpentine, belongs to a special class of natural olefins with a bicyclic substituent [ 25 , 26 ].…”

“…[ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ] and references therein). Beyond doubt, β-pinene, which is the most abundant commercial terpene and is obtained from turpentine, belongs to a special class of natural olefins with a bicyclic substituent [ 25 , 26 ]. The reactive exo methylene group in β-pinene makes it able to undergo carbocationic, and to a certain extent radical and coordinative polymerizations.…”

Scalemic natural products

“…1 The existence of racemic natural products, that is of an equimolar mixture of both enantiomers in a single producer, was actually rst reported with compounds better referred to as racemized rather than racemic, since loss of enantiomeric purity had occurred during extraction and/or isolation, as in paratartaric (racemic) acid ((AE)-2) 2 and atropine ((AE)-3), 3 but truly racemic natural products were then shown to exist, and certain biogenetic pathways are now recognized to be signicantly associated to the generation of racemic natural products. 4 More puzzling is the occurrence of scalemic (enantiomerically enriched) natural products, not only simple monoterpenes like a-pinene (1), known to occur as (+)-, (−)-, (±)-a-pinene as well as in various ratios of its enantiomers, 5 but also more complex and polycyclic compounds like the meroterpene cis-D 9 -tetrahydrocannabinol (4) 6 and the alkaloid cephalotaxine (5). 7 The number of these occurrences increased with the advent of chiral HPLC as routine analytical tool for natural product mixture.…”

“…Oxidative modication of isoprenoid residues 3.2. 5 Functionalization of non-isoprenyl unactivated carbons 3.2. 6 Cycloaddition reactions 4…”

Ti3C2 MXenes-based catalysts for the process of α-pinene isomerization

“…a-Pinene is also found in essential oils obtained from pine, rosemary, cumin, thyme, basil, eucalyptus, and orange peels. [3][4][5] a-Pinene is of great interest to scientists due to its biologically active properties (it is used as a fragrance in cosmetics, and in medicine for the treatment of respiratory infections or dissolution of kidney stones), as well as due to the possibility of obtaining derivatives of this terpene compound which also have numerous applications, including applications in medicine. The great advantage of a-pinene as the raw material for organic syntheses is that it is a relatively easily available and cheap raw material, and above all reproducible.…”