Eastern white cedar

Occidentalol (628), a eudesmane-type sesquiterpene isolated from the wood of Eastern white cedar, was synthesized from a as-fused decalin system (627) prepared by cycloaddition of the a-pyrone (625) with 4-methyl-3-cyclohexenone (626 Scheme 140) (72TL4651). Derivatives of 2-pyrone have also been employed in syntheses of colchicine (629 Scheme 141) (59AG637) and barrelene (630 Scheme 142) (69JA2330). 

Bark from eastern white cedar and western redcedar was used as the entire furnish, or with a mixture of 10% pulp screenings. These species were chosen because of the natural fibrous nature of their barks. Although tests showed the experimental hardboards could not meet standards then in force, eastern white cedar bark showed some promise. For softboards, the eastern white cedar produced acceptable boards. 

One step in the synthesis of occidentaioi, a naturai product isoiated from the eastern white cedar tree, involved the foiiowing reaction, identify the structure of A and show how A is converted to B. 

CARTIER, A., CHAN, H MALO, J-L., PINEAU, L TSE, K.S. CHAN-YEUNG, M. (1986) Occupational asthma caused by eastern white cedar (Thuja occidentalis) with demonstration that plicatic acid is present in this wood dust and is the causal agent. Journal of Allergy and Clinical Immunology, 77, 639-645. 

Young leafy twigs used against some types of cancer. Commonly removes warts. Known as an abortifacient. Also called eastern arborvitae, eastern white cedar, northern white cedar, swamp cedar, tree of life. 

Northern or Eastern White Cedar Thuja occidentalis L... 

OCN eastern white cedar eastern arborvitae northern white cedar swamp cedar... 

Black willow (Salix nigra March.) 21 Eastern white cedar (Thuja occidentalis) 31... 

Roy D N, Konar S K, Purdy J R 1984 Sublimation of occidentalol, a sesquiterpene alcohol from eastern white cedar Thuja occidentalis L.) in a drying kiln. Can J For Res 14 401-411... 

One of the problems is that compounds are not accumulated in cells but are released into the culture medium where they are lost, if volatile, or may interfere biologically with subsequent cell growth and division. This problem has been dealt within cell cultures of Thuja occidentalis (eastern white cedar) by Berlin and co-workers (4) by adding an insoluble solvent trap to collect terpenes and tropo-lones released into the medium. The yield of thujaplicins was nearly tripled over the duration of the fermentation by this technique. Nevertheless, the secondary metabolite generated by the Thuja cultures did not replicate what might be expected from any specific part of the tree. 

Occidentalol is a eudesmane-type sesquiterpene isolated from the wood of Eastern white cedar Thuja occldentalis Linn.), and is characterized by the presence of a c/s-fused decalin system and a homoannular 1,3-diene unit in the molecule, an intriguing combination of functional groups rarely encountered in this class of natural products. Three related syntheses of occidentalol, all of which are based on hexahydronaphthalen-2-one intermediates have been reported, and utilize the carbonyl group for introduction of the diene chromophore in ring A 1-3,5 synthesis outlined below, utilizing a c/s-fused decalone derivative (A) illustrates several of the key features of these syntheses. 

Joints bonded with casein glue will average better than 90% wood failure when the following softer wood species are used redwood, western red cedar, white fir, Sitka spruce, southern cypress, western hemlock, eastern red cedar, chestnut, red alder, and northern white pine. With the harder woods—red oak, maple, white ash, yellow birch, and persimmon—the joints will show 30-50% wood failure. 

Even that kind of information is not available for forest species. Other than chronic injury to white pine (associated with ozone, sulfur dioxide, and their mixtures), no clearly defined examples of chronic injury from ozone have been reported for eastern forests, and no information is available on PAN. It is of interest that both Virginia and jack pine appear more sensitive than white pine to acute ozone exposures, but chronic symptoms have not been observed in either species. The relationship between oxidant dose and injury in the San Bernardino Mountains area suggests that ponderosa pine is moderately to severely injured in areas that receive oxidant at above 0.08 ppm for 12-13 h each day (Chapter 12). Ponderosa pine seems to be the most sensitive western pine, but in some areas Jeffrey pine is about as sensitive. White fir, incense cedar, and sugar pine all appear more tolerant, even to the high oxidant concentrations in the San Bernardino Mountains. PAN may play some role in the chronic responses noted in the western forest species, particularly by broadleaf deciduous trees and some shrubs. 

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