Caryophyllen 3 epoxy

A new elegant stereoselective synthesis of humulene (192) has been achieved by a route (Scheme 22) in which the 11-membered-ring framework [cf. (191)] is produced by cyclization of the 11-allylpalladium complex derived from intermediate (190). Buddledin-A (193), -B (194), and -C (195) are new piscicidal sesquiterpenoids which have recently been isolated from the root bark of Buddleja davidiC The caryophyliane framework of these compounds has been established by spectroscopic data and X-ray analysis of the mono-bromohydrin (196) derived from buddledin A (193). An extension of previous studies on the cyclization of the epoxy-ketone (197) derived from caryophyllene has shown that the base-catalysed cyclization of the isomeric epoxy-ketones (198) and (199) provides compounds... 

Cyclic epoxide derivatives, such as 2,3-epoxy-c/s-pinane 210 [Eq. (5.299)]826 and isomeric caryophyllene diepoxides 211 [Eq. (5.300)],827 undergo varied transformations including ring contraction under similar conditions. 

Earlier workers established the presence of a-pinene, (3-pinene, 1-a-phellandrene, dl-limonene, piperonal, dihydrocarveol, a compound melting at 161°C, P-caryophyllene and a piperidine complex from the essential oil obtained by steam distillation of ground Malabar pepper. The above compounds were identified by the classical methods of derivatization and degradation. They also reported the presence of epoxy dihydrocary-... 

About 20 oxygenated sesquiterpenes have been identified from pepper oil. They are 5,10(15)-cadinen-4-ol,caryophylla-3(12), 7(15)-dien-4-P-ol, caryophylla-2,7(15)-dien-4- 3-ol, caryophylla-2,7(15)-dien-4-ol, P-caryophellene alcohol, caryophyllene ketone, caryophellene oxide, epoxy-dihydrocaryophellene, cis-nero-lidol, 4,10,10-trimethyl-7-methylene bicycle-(6.2.0) decane-4-carboxaldehyde, cubenol, epi-cubenol, viridiflorol, a- and P-bisabolols, cubebol, elemol and y-eudesmol. 

SYNS CARYOPHYLLENE EPOXIDE CARYOPHYLLENE OXIDE (-)-CARYOPHYLLENE OXIDE P-CARYOPHYLLENE OXIDE EPOXY-CARYOPHYLLENE (-)-EPOXYDIHYDROCARY-OPHYLLENE 5-OXATRICYCLO(8.2.0.0 > DODECANE, 4,12,12-TRIMETHYL-9-METHYLENE-, (1R,4R,6R,10S)- 4.11.11-TRIMETHYL-8-METHYLENE-50XATRI-CYCL0-(8.2.0.0(4,6))DODECANE... 

Caryophyllene oxide (1-S-5c-6t-epoxy-6c,10,10-trimethyl-2-methylene-lr,9t-bicyclo-... 

Other representatives include (-)-6,7-epoxy-3(15)-caryophyllene from the leaves, flowers and stems of cloves, (+)-6-caryophyllen-15-al from the oil of sage (Salvia sclarea, Labiatae), and (-)-3(15),7-caryophylladien-6-ol from Indian hemp Cannabis saliva var. indica (Cannabaceae). 

See P-Caryophyllene Methylenium ceruleum. See Basic blue 9 Methyl epi-jasmonate. See Methyl jasmonate Methyl epoxy soyate. See Epoxiidized soybean oil, methyl ester... 

An example of terpenic 1,2-epoxides is -caryophyllene oxide, also known as (-)-epoxycaryophyllene (8-31), which occurs in many essential oils. An example of terpenic 1,4-epoxides is the so-called (-l-)-dill ether, (3J ,4S,8S)-3,9-epoxy-p-menth-l-ene (8-31), which is a typical component of the essential oil of caraway (30%) and dill. An example of unsaturated 1,4-epoxides is (-l-)-menthofuran (8-31), the metabolite of ketone (-l-)-pulegone. Both compounds are components of peppermint oil (see Table 8.32, later) and are hepatotoxic. Monoterpenoid compound (- -)-l,8-cineole (also known as limonene oxide, eucalyptol or 1,8-epoxy-p-menthane 8-31) is an example of more complex structures. It is present in essential oils of many types of spices, and higher quantities are found in the essential oil of trees of the genus Eucalyptus (Myrtaceae). Trivial and systematic names of selected ethers are given in Table 8.8. 

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