- Total synthesis and structural confirmation of the antibacterial diterpene leubethanol
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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
- Lu, Jessica M.H.,Perkins, Michael V.,Griesser, Hans J.
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p. 6468 - 6473
(2013/07/26)
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- Cyclopropenium-activated cyclodehydration of diols
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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.
- Kelly, Brendan D.,Lambert, Tristan H.
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supporting information; experimental part
p. 740 - 743
(2011/05/04)
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- Hydroxylation of (+)-menthol by Macrophomina phaseolina
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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.
- Musharraf, Syed Ghulam,Ahmed, Muhammad Arif,Ali, Rahat Azher,Choudhary, Muhammad Iqbal
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experimental part
p. 77 - 82
(2012/04/11)
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- Regioselective free radical phenylsulfenation of a non-activated δ-carbon atom by the photolysis of alkyl benzenesulfenate
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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
- Petrovi?, Goran,Sai?i?, Radomir N.,?ekovi?, ?ivorad
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p. 187 - 196
(2007/10/03)
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- Enzyme-mediated preparation of enantiomerically pure p-menthan-3,9-diols and their use for the synthesis of natural p-menthane lactones and ethers
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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).
- Serra, Stefano,Fuganti, Claudio
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p. 2489 - 2502
(2007/10/03)
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- Synthesis and organoleptic properties of p-menthane lactones
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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
- Gaudin, Jean-Marc
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p. 4769 - 4776
(2007/10/03)
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- Pheromone syntheses: A tropical approach. Enantioselective synthesis of the (2R,6S,10S) and (2S,6S,10S) isomers of methyl 2,6,10-trimethyldodecanoate
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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
- Ferreira, J. Tercio B.,Zarbin, Paulo H. G.
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p. 381 - 388
(2007/10/03)
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- A novel asymmetric total synthesis of (+)-artemisinin
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A 12-step synthesis of the natural product (+)-Artemisinin, very active against malaria, is described. (-)-Isopulegol, which already contains two of the asymmetric centers of (+)-Artemisinin in the correct absolute configuration, was used as starting material.
- Constantino, Mauricio Gomes,Beltrame Jr., Milton,De Silva, Gil Valdo Jose,Zukerrnan-Schpector, Julio
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p. 321 - 329
(2007/10/03)
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- Synthesis and Transformations of (+/-)-trans-4aβ(H),8aα(H)-Octahydro-4α,7β-dimethyl-2H-1-benzopyran-2-one
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Hydrogenation of 4,7-dimethylcoumarin (1) in alkaline medium has been shown to furnish a mixture of (+/-)-trans-4aβ(H),8aα(H)-octahydro-4α,7β-dimethyl-2H-1-benzopyran-2-one (2), (+/-)-trans-4aβ(H),8aα(H)-octahydro-4α,7α-dimethyl-2H-1-benzopyran-2-one (3)
- Sanghvi, Y. S.,Rao, A. S.
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p. 1377 - 1380
(2007/10/02)
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