Search results for "Carvone"
showing 10 items of 10 documents
Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone
2005
Abstract The synthesis of the spirocyclic sesquiterpenes (−)-gleenol and (−)-axenol in enantiomerically pure form has been achieved starting from R-(−)-carvone. The key step is the silicon guided acid-promoted rearrangement of a 9-trimethylsilyl-5,6-epoxy-noreudesmane prepared from 3-trimethylsilyldihydrocarvone in several steps involving Robinson annulation, enone deconjugation and epoxidation. Acid treatment of the epoxy-noreudesmane gave a norspiroaxane as the main product, which was used as intermediate for the synthesis of two naturally occurring sesquiterpenes gleenol and axenol.
Can foliar-applied nutrients improve caraway (Carum carvi L.) seed oil composition?
2021
Caraway seeds contain between 0.5–7% essential oil, rich in monoterpenes that have a characteristic aroma and chemical properties. Caraway oil has several bioactive compounds that are of industrial importance, particularly for pharmaceutical and health care products. Carvone and limonene are the main terpenes present in caraway oil, which along with some unique fatty acids (i.e. petroselinic acid) determine caraway (Carum carvi L.) oil quality. Both terpenes are important raw materials for industrial applications and their concentration influences the price of caraway seed and oil, hence there is need for identifying management practices that may increase the concentration of these and othe…
Synthesis of oxygenated spongiane-type diterpenoids from carvone
2002
Abstract A new diastereoselective approach to oxygenated spongiane diterpenes starting from ( R )-(−)-carvone is described. The carvone is incorporated as the B ring in the final spongiane framework using a B→AB→ABC→ABCD approach, which involves an intramolecular Diels–Alder reaction and the regioselective ring-opening of a dihydrofuran ring as key synthetic steps. The structure of the key intermediate in this approach has been verified by X-ray crystallography.
Synthetic studies on the preparation of oxygenated spongiane diterpenes from carvone
2003
Abstract The paper describes a new diastereoselective approach to oxygenated spongiane diterpenes functionally related to natural dorisenones. The strategy followed for the preparation of the spongiane framework, a B→AB→ABC→ABCD approach, is based on the preparation of epoxydecalone 11 (AB rings) from R-(−)-carvone, followed by an intramolecular Diels–Alder reaction for the construction of the C ring (compound 26 ). Further manipulation of the Diels–Alder adduct functionality allows the completion of the spongiane framework and the elaboration of several oxygenated spongiane-type compounds. The structures of two compounds 27 and 31 , has been established by single-crystal X-ray crystallogra…
The Antigerminative Activity of Twenty-Seven Monoterpenes
2010
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ChemInform Abstract: Stereoselective Construction of the Tetracyclic Scalarane Skeleton from Carvone.
2010
The tetracyclic scalarane skeleton 22 has been constructed from (S)-(+)-carvone using two intramolecular Diels–Alder reactions as key synthetic steps.
Syntheses of oxygenated spongiane diterpenes from carvone. Synthesis of dorisenone C
2005
Abstract The synthesis of dorisenone C, a representative member of the spongiane-type diterpene family, is described. The synthesis follows a B→AB→ABC→ABCD approach and is based on the initial preparation of the previously known hydroxy-aldehyde 14 (AB rings) from R -(−)-carvone, followed by an intramolecular Diels–Alder reaction between an oxygenated diene moiety and an acetylenic dienophile for the construction of the C ring (compound 22 ), and adequate manipulation of the Diels–Alder adduct functionality for completion of the spongiane framework.
A molecular electron density theory study of the mechanism, chemo- and stereoselectivity of the epoxidation reaction of R -carvone with peracetic acid
2019
The epoxidation reaction of R-carvone 8 with peracetic acid 9 has been studied within the molecular electron density theory at the B3LYP/6-311(d,p) computational level. The chemo- and stereoisomeric reaction paths involving the two C–C double bonds of R-carvone 8 have been studied. DFT calculations account for the high chemoselectivity involving the C–C double bond of the isopropenyl group and the low diastereoselectivity, in complete agreement with the experimental outcomes. The Baeyer–Villiger reaction involving the carbonyl group of R-carvone 8 has also been analysed. A bonding evolution theory analysis of the epoxidation reaction shows the complexity of the bonding cha…
Syntheses of Oxygenated Spongiane Diterpenes from Carvone. Synthesis of Dorisenone C.
2005
Abstract The synthesis of dorisenone C, a representative member of the spongiane-type diterpene family, is described. The synthesis follows a B→AB→ABC→ABCD approach and is based on the initial preparation of the previously known hydroxy-aldehyde 14 (AB rings) from R -(−)-carvone, followed by an intramolecular Diels–Alder reaction between an oxygenated diene moiety and an acetylenic dienophile for the construction of the C ring (compound 22 ), and adequate manipulation of the Diels–Alder adduct functionality for completion of the spongiane framework.
Stereoselective construction of the tetracyclic scalarane skeleton from carvone
1999
The tetracyclic scalarane skeleton 22 has been constructed from (S)-(+)-carvone using two intramolecular Diels–Alder reactions as key synthetic steps. Abad Somovilla, Antonio, Antonio.Abad@uv.es ; Agullo Blanes, M Consuelo, Consuelo.Agullo@uv.es ; Cuñat Romero, Ana Carmen, Ana.Cunat@uv.es ; Llosa Blasco, Maria Carmen, Carmen.Llosa@uv.es