37267-80-4Relevant articles and documents
Anodic coupling reactions: probing the stereochemistry of tetrahydrofuran formation. A short, convenient synthesis of linalool oxide.
Duan,Moeller
, p. 2685 - 2688 (2001)
[reaction: see text]. Intramolecular coupling reactions between enol ether radical cations and oxygen nucleophiles are primarily governed by stereoelectronics. By taking advantage of this observation, a tetrahydrofuran building block for use in constructing (+)-linalool oxide and rotundisine has been synthesized in four steps from a commercially available starting material. The synthesis of (+)-linalool oxide has been completed.
VOLATILE OIL CONSTITUENTS OF SAGEBRUSH
Epstein, William W.,Gaudioso, Larry A.
, p. 2257 - 2262 (1984)
The volatile oil of Artemisia arbuscula arbuscula contained a new irregular monoterpene, 2,5-dimethyl-4-vinyl-1,5-hexadiene-3-ol (isolyratol), which was isolated and identified by spectral means.The optically pure furanoid (2S,5S)-trans-5-methyl-5-vinyltetrahydrofur-2-yl methyl ketone (arbusculone), was also characterized by transformation to known (2S,5S)-trans-linalyl oxide.The former component has never been isolated from natural sources prior to this study.The neutral pentane extract also contained several previously characterized non-head-to-tail monoterpenes including artemiseole, artemisia ketone, artemisyl acetate, methyl santolinate, and santolina triene, as well as the regular monoterpenes 1,8-cineole, camphor, p-cymene, camphene and the C6 fragment, terelactone. - Key Word Index: Artemisia arbuscula arbuscula; Asteraceae (Compositae); volatile oil; monoterpenes; irregular monoterpenes.
Enantioselective Bio-Hydrolysis of Geranyl-Derived rac-Epoxides: A Chemoenzymatic Route to trans-Furanoid Linalool Oxide
van Lint, Matthijs J.,Gümüs, Aysegül,Ruijter, Eelco,Faber, Kurt,Orru, Romano V. A.,Hall, Mélanie
, p. 813 - 825 (2019/01/04)
In contrast to many chemical dihydroxylation methods, enzymatic epoxide hydrolysis provides an environmentally benign route to vicinal diols, which are important intermediates in the synthesis of fine chemicals and pharmaceuticals. Using epoxide hydrolases, enantiopure diols are accessible under mild conditions. In order to assess the selectivity of epoxide hydrolases on geraniol-derived oxiranes, a range of derivatives were screened against a large variety of enzyme preparations. For nearly all substrates, a matching hydrolase with excellent enantioselectivity (≥95% ee) could be found. In addition, a chemoenzymatic approach for the stereoselective synthesis of furanoid linalool oxide was developed. Combination of enzymatic enantioselective hydrolysis with stereoselective Tsuji-Trost reaction granted diastereoselective access to trans-(2R,5R)-configured linalool oxide with high diastereomeric and enantiomeric excess (97% de and 97% ee). (Figure presented.).
Asymmetric synthesis and structure-activity studies of the fungal metabolites colletorin A, colletochlorin A and their halogenates analogues
Marsico, Giulia,Pignataro, Barbara A.,Masi, Marco,Evidente, Antonio,Casella, Francesca,Zonno, Maria Chiara,Tak, Jun-Hyung,Bloomquist, Jeffrey R.,Superchi, Stefano,Scafato, Patrizia
, p. 3912 - 3923 (2018/06/08)
The first asymmetric total synthesis of both enantiomers of the natural products colletorin A and colletochlorin A is presented. The proposed methodology is based on the coupling reaction between highly substituted aromatic Gilman cuprates and optically active allyl bromides, in turn obtained by Sharpless asymmetric dihydroxylation. The latter ensured a high degree of regio- and stereocontrol in the enantioselective step of the synthesis. The same synthetic strategy has been also applied for the preparation of differently halogenated synthetic analogues of colletochlorin A in high enantiomeric purity. The enantioselective synthesis of colletorin A and colletochlorin A allows to reliably assign their absolute configuration. Preliminary assessment of their herbicidal and insecticidal properties evidence the possibility to modulate the bioactivity of these compounds, highlighting its dependence on both the absolute stereochemistry and the halogen nature.
