13834-07-6Relevant articles and documents
Asymmetric synthesis of dihydroartemisinic acid through intramolecular Stetter reaction
Rej, Rohan Kalyan,Acharyya, Ranjan Kumar,Nanda, Samik
, p. 4931 - 4937 (2016/07/19)
A short and concise formal synthesis of enantiopure dihydroartemisinic acid from (R)-citronellal is described in this article. Intramolecular version of asymmetric Stetter reaction using Rovis aminoindane based NHC catalyst was explored to access the core
Total synthesis and structural confirmation of the antibacterial diterpene leubethanol
Lu, Jessica M.H.,Perkins, Michael V.,Griesser, Hans J.
, p. 6468 - 6473 (2013/07/26)
We report the total synthesis of leubethanol (1), a serrulatane compound that has recently been reported as having considerable antibacterial activity against multidrug-resistant bacteria, such as Staphylococcus aureus, and is of interest for applications
Cyclopropenium-activated cyclodehydration of diols
Kelly, Brendan D.,Lambert, Tristan H.
supporting information; experimental part, p. 740 - 743 (2011/05/04)
The dehydrative cyclization of diols to cyclic ethers via cyclopropenium activation is described. Using 2,3-diphenylcyclopropene and methanesulfonic anhydride, a series of 1,4-and 1,5-diols are rapidly cyclized to furnish tetrahydrofurans and tetrahydropyrans in high yield. Eleven total substrates are shown, including a gram scale cyclization of a diterpene derivative.
Hydroxylation of (+)-menthol by Macrophomina phaseolina
Musharraf, Syed Ghulam,Ahmed, Muhammad Arif,Ali, Rahat Azher,Choudhary, Muhammad Iqbal
experimental part, p. 77 - 82 (2012/04/11)
Biotransformation of (+)-menthol with Macrophomina phaseolina led to hydroxylations at C-1, C-2, C-6, C-7, C-8 and C-9, with the C-8 position being preferentially oxidized. The resulting metabolites were identified as 8-hydroxymenthol (2), 6R-hydroxymenthol (3), 1R-hydroxymenthol (4), 9-hydroxymenthol (5), 2R,8-dihydroxymenthol (6), 8S,9-dihydroxymenthol (7), 6R,8-dihydroxymenthol (8), 1R,8-dihydroxymenthol (9) and 7,8-dihydroxymenthol (10). Metabolites 6-10 are described here for the first time. Their structures were characterized by spectroscopic analysis.
Enantioselective synthesis of three stereoisomers of 5,9- dimethylpentadecane, sex pheromone component of Leucoptera coffeella, from (-)-isopulegol
Moreira, Jardel A.,Correa, Arlene G.
, p. 3787 - 3795 (2007/10/03)
The coffee leaf miner, Leucoptera coffeella, is an economically important pest of coffee trees in Brazil. It has been demonstrated that the main sex pheromone component of this species is 5,9-dimethylpentadecane, however the stereochemistry of the natural
Regioselective free radical phenylsulfenation of a non-activated δ-carbon atom by the photolysis of alkyl benzenesulfenate
Petrovi?, Goran,Sai?i?, Radomir N.,?ekovi?, ?ivorad
, p. 187 - 196 (2007/10/03)
A regioselective free radical introduction of a phenylthio group onto a non-activated δ-carbon atom was achieved by photolysis of alkyl benzenesulfenates in the presence of hexabutylditin, and δ-phenylthio alcohols were obtained in 35-91% yields. δ-Phenyl
Enzyme-mediated preparation of enantiomerically pure p-menthan-3,9-diols and their use for the synthesis of natural p-menthane lactones and ethers
Serra, Stefano,Fuganti, Claudio
, p. 2489 - 2502 (2007/10/03)
The diastereoselective preparation of the p-menthane-3,9-diols (±)-12, (±)-13a, (±)-13b, and (±)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).
Synthesis and organoleptic properties of p-menthane lactones
Gaudin, Jean-Marc
, p. 4769 - 4776 (2007/10/03)
The stereoselective synthesis and organoleptic properties of p-menthane lactones 7a-h are described. Apart from correcting the published data concerning these compounds, this work has also allowed an unambiguous identification of 7a, 7b and 7g in Italo Mi
Stereospecific synthesis of (-)-β-turmerone and (-)-bisacurol
Kreiser, Wolfgang,Koerner, Ferdinand
, p. 1610 - 1629 (2007/10/03)
The structure of (+)-β-turmerone ((+)-1a), a constituent of the rhizomes of Curcuma longa LINN., and Curcuma xanthorriza, is established as (1'R,6S)-2-methyl-6-(4'-methylenecyclohex-2'-en-1'-yl)hept-2-en-4-one by synthesis of its enantiomer (-)-1a, and of
Pheromone syntheses: A tropical approach. Enantioselective synthesis of the (2R,6S,10S) and (2S,6S,10S) isomers of methyl 2,6,10-trimethyldodecanoate
Ferreira, J. Tercio B.,Zarbin, Paulo H. G.
, p. 381 - 388 (2007/10/03)
The enantioselective syntheses of two stereoisomers, (2R,6S,10S) and (2S,6S,10S), of methyl 2,6,10-trimethyldodecanoate, out of eight possible isomers, are described, employing the stereoselective hydroboration of (-)-isopulegol (2) and (+)-neo-isopulegol
