287720-47-2Relevant articles and documents
Biosynthesis of Stereoisomers of Dill Ether and Wine Lactone by Pleurotus sapidus
Trapp, Tobias,Kirchner, Tabea,Birk, Florian,Fraatz, Marco Alexander,Zorn, Holger
, p. 13400 - 13411 (2019/03/26)
The white-rot fungus Pleurotus sapidus (PSA) biosynthesizes the bicyclic monoterpenoids 3,6-dimethyl-2,3,3a,4,5,7a-hexahydrobenzofuran (dill ether) (1) and 3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one (wine lactone) (2). Submerged cultures gro
Photocaged Hydrocarbons, Aldehydes, Ketones, Enones, and Carboxylic Acids and Esters that Release by the Norrish II Cleavage Protocol and Beyond: Controlled Photoinduced Fragrance Release
Griesbeck, Axel G.,Porschen, Bj?rn,Kropf, Christian,Landes, Agnieszka,Hinze, Olga,Huchel, Ursula,Gerke, Thomas
, p. 539 - 553 (2017/01/25)
Five families of caged fragrance compounds that allow the storage and release of the following small volatile organic molecules are described: terpene hydrocarbons, aldehydes, ketones, Michael-type α,β-unsaturated enones, and carboxylic acids and esters. These caged molecules are released by photoexcitation via carbonyl-directed hydrogen-transfer processes and subsequent C-C bond cleavage (Norrish Type II) or by didenitrogenation of diazirines.
TERPENE AND TERPENOID DERIVATIVES CONTAINING VINYL GROUPS FOR THE PREPARATION OF POLYMERS
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Page/Page column 47; 55, (2015/11/10)
The invention relates to a method for producing functionalised monomers, the method comprising: a) providing a starting material selected from terpenes and terpenoids; b) forming a derivative of the starting material by incorporation of a hydroxyl group; c) esterifying the hydroxyl group of the derivative to introduce a moiety containing a vinyl group, so as to produce a functionalised monomer. The functionalised monomer can be polymerised to obtain a bio-derived polymer.
Highly regio- and enantioselective catalytic asymmetric hydroboration of α-substituted styrenyl derivatives
Mazet, Clement,Gerard, David
supporting information; scheme or table, p. 298 - 300 (2011/02/24)
The catalytic asymmetric hydroboration of a variety of 1,1-disubstituted olefins has been achieved with excellent yields, perfect regioselectivity and in some cases, high levels of enantioselectivity using readily accessible iridium catalyst.
A chemoenzymatic, preparative synthesis of the isomeric forms of p-menth-1-en-9-ol: Application to the synthesis of the isomeric forms of the cooling agent 1-hydroxy-2,9-cineole
Serra, Stefano,Fuganti, Claudio,Gatti, Francesco G.
experimental part, p. 1031 - 1037 (2009/04/05)
A preparative-scale synthesis of the four p-menth-1-en-9-ol isomers 2a-5a has been achieved by means of two chemoenzymatic processes. Both synthetic pathways start from the enantiomeric forms of limonene that are converted into p-mentha-1,8-dien-9-al isomers 12 and 15. The baker's yeast mediated reduction of the latter aldehydes afforded compounds 3a and 5a, respectively, with very high enantioselectivity. Moreover, chemical reduction of 12 and 15 gives the mixtures of enantiopure diastereoisomers 2a/3a and 4a/5a, respectively. PPL (Porcine pancreas lipase) mediated resolution of the latter mixtures followed by fractionating crystallization of derivatives 2b-5b allowed the enantio- and diastereoisomerically pure alcohols 2a-5a to be obtained. Compounds 2a-5a have then been used as starting materials for the preparation of four isomers of the cooling agent 1-hydroxy-2,9-cineole (6-9). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
PS-COD and PS-9-BBN: Polymer-supported reagents for solution-phase parallel synthesis
Revell, Jefferson D.,Doerner, Barbara,White, Peter D.,Ganesan
, p. 831 - 833 (2007/10/03)
(Chemical Equation Presented) 1,5-Cyclooctadiene was deprotonated under LICKOR conditions and reacted with Merrifield resin to afford an immobilized cyclooctadiene in high yield. This polymer is effective as a halogen scavenger, while hydroboration leads to a supported 9-BBN analogue. The latter exhibits similar regioselectivity to 9-BBN in olefin hydroboration.
Convergent approaches to saudin intermediates
Cravero, Raquel M.,Gonzalez-Sierra, Manuel,Labadie, Guillermo R.
, p. 2741 - 2753 (2007/10/03)
Different convergent approaches to the highly oxygenated sesquiterpene natural product saudin (1), has been investigated. Our strategy has included a Michael addition and aldol condensation reaction as key steps. During the synthetic development, we have found serious steric hindrance when an α-Me-substituted alkyl vinyl ketone was used. Such steric hindrance has been overcome by synthesizing the vinyl ketone 16 through an anionic fragmentation, which was carefully studied. Finally, the intermediate 18 has been synthesized in a one-pot reaction from the vinyl ketone 16 and has been cyclized to obtain the promising tricyclic intermediate 20.
131. Determination of the configuration of wine lactone
Guth, Helmut
, p. 1559 - 1571 (2007/10/03)
The intense sweet and coconut-like smelling odorant 1, named 'wine lactone', was isolated from different wine varieties. The chemical structure of this compound, which has not yet been detected in wine or a food, was identified by high-resolution mass spe
Benzyl 2,3-O-isopropylidene-β-D-ribo-1,4-pentodialdofuranoside as a D-Ribose Chiron for the Synthesis of Terpenyl Tetraols and Aminotriols
Duvold, Tore,Francis, George W.
, p. 3153 - 3156 (2007/10/02)
Wittig condensation of title compound with a phosphorane derived from R-(+)-limonene followed by catalytic hydrogenation, provided a C-5 extended ribofuranose derivative, a model intermediate for the synthesis of terpenyl tetraols, via NaBH4 reduction, an
