- Monoterpene glycosides and triterpene acids from Eriobotrya deflexa
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A phytochemical study on a methanolic extract of leaves of Eriobotrya deflexa led to the isolation and characterization of nine terpenoid compounds. Four of these are new chemical entities, including two monoterpene glycosides, (3S)-O-α-L-rhamnopyranosyl-(1→3)-[4-O-(E)-coumaroyl]- α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-linalool (1) and (3S)-O-α-L-rhamnopyranosyl-(1→3)-[4-O-(Z)-coumaroyl]-α-L- rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-linalool (2), and two triterpene acids, 1β,2α,19α-trihydroxy-3-oxo-12-ursen-28-oic acid (3) and 2α,3α,19α-trihydroxy-12-oleanen-28-oic acid (4). Their structures were elucidated on the basis of spectroscopic analysis. The activities of these isolates in an in vitro antiproliferation test were also determined.
- Lee,Lee,Kuo,Chou
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- 1,3-Transposition of primary allylic alcohols: Synthesis of optically active secondary and tertiary allylic alcohols
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The reduction of optically active 2,3-epoxy alcohols, suitably prepared by the Sharpless asymmetric epoxidation of primary allylic alcohols, with the system triphenylphosphine/ iodine/imidozole/2,6-lutidine/water, leads in a single step to optically active secondary and tertiary allylic alcohols.
- Dorta, Rosa L.,Rodriguez, Maria S.,Salazar, Jose A.,Suarez, Ernesto
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- Exploring castellaniella defragrans linalool (De)hydratase-isomerase for enzymatic hydration of alkenes
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Acyclic monoterpenes constitute a large and highly abundant class of secondary plant metabolites and are, therefore, attractive low-cost raw materials for the chemical industry. To date, numerous biocatalysts for their transformation are known, giving access to highly sought-after monoterpenoids. In view of the high selectivity associated with many of these reactions, the demand for enzymes generating commercially important target molecules is unabated. Here, linalool (de)hydratase-isomerase (Ldi, EC 4.2.1.127) from Castellaniella defragrans was examined for the regio- and stereoselective hydration of the acyclic monoterpene β-myrcene to (S)-(+)-linalool. Expression of the native enzyme in Escherichia coli allowed for identification of bottlenecks limiting enzyme activity, which were investigated by mutating selected residues implied in enzyme assembly and function. Combining these analyses with the recently published 3D structures of Ldi highlighted the precisely coordinated reduction–oxidation state of two cysteine pairs in correct oligomeric assembly and the catalytic mechanism, respectively. Subcellular targeting studies upon fusion of Ldi to different signal sequences revealed the significance of periplasmic localization of the mature enzyme in the heterologous expression host. This study provides biochemical and mechanistic insight into the hydration of β-myrcene, a nonfunctionalized terpene, and emphasizes its potential for access to scarcely available but commercially interesting tertiary alcohols.
- Engleder, Matthias,Müller, Monika,Kaluzna, Iwona,Mink, Daniel,Schürmann, Martin,Leitner, Erich,Pichler, Harald,Emmerstorfer-Augustin, Anita
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- Metal-organic framework Co(D-cam)1/2(bdc)1/2(tmdpy) for improved enantioseparations on a chiral cyclodextrin stationary phase in gas chromatography
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Initial efforts to combine a chiral metal-organic framework (MOF), Co(D-Cam)1/2(bdc)1/2(tmdpy) (D-Cam=D-camphoric acid, bdc=1,4-benzenedicarboxylic acid, tmdpy=4,4′-trimethylenedipyridine), with peramylated β-cyclodextrins to investigate whether the use of a MOF can enhance enantioseparations on a cyclodextrin stationary phase are reported. Compared with columns of peramylated β-cyclodextrin incorporated in a MOF containing sodium chloride, the column of peramylated β-cyclodextrin+MOF shows excellent selectivity for the recognition of racemates, and higher resolutions are achieved on the peramylated β-cyclodextrin+MOF stationary phase. Experimental results indicate that the use of Co(D-Cam) 1/2(bdc)1/2(tmdpy) can improve enantioseparations on peramylated β-cyclodextrins. This is the first report that chiral MOFs can improve enantioseparations on a chiral stationary phase for chromatography. Copyright
- Liu, Hong,Xie, Sheng-Ming,Ai, Ping,Zhang, Jun-Hui,Zhang, Mei,Yuan, Li-Ming
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p. 1103 - 1108
(2014/11/07)
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- Transcriptome profiling, and cloning and characterization of the main monoterpene synthases of Coriandrum sativum L.
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Terpenoids are a large and diverse class of specialized metabolites that are essential for the growth and development of plants, and have tremendous industrial applications. The mericarps of Coriandrum sativum L. (coriander) produce an essential oil (EO) rich in monoterpenes, volatile C10 terpenoids. To investigate EO metabolism, the transcriptome of coriander mericarps, at three developmental stages (early, mid, late) was sequenced via Illumina technology and a transcript library was produced. To validate the usability of the transcriptome sequences, two terpene synthase candidate genes, CsγTRPS and CsLINS, encoding 558 and 562 amino acid proteins were expressed in bacteria, and the recombinant proteins purified by Ni-NTA affinity chromatography. The 65.16 (CsγTRPS) and 65.91 (CsLINS) kDa recombinant proteins catalyzed the conversion of geranyl diphosphate, the precursor to monoterpenes, to γ-terpinene and (S)-linalool, respectively, with apparent Vmax and Km values of 2.24 ± 0.16 (CsγTRPS); 19.63 ± 1.05 (CsLINS) pkat/mg and 66.25 ± 13 (CsγTRPS); 2.5 ± 0.6 (CsLINS) μM, respectively. Together, CsγTRPS and CsLINS account for the majority of EO constituents in coriander mericarps. Investigation of the coriander transcriptome, and knowledge gained from these experiments will facilitate future studies concerning essential and fatty acid oil production in coriander. They also enable efforts to improve the coriander oils through metabolic engineering or plant breeding.
- Galata, Mariana,Sarker, Lukman S.,Mahmoud, Soheil S.
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- Synthesis and reactions of the optically active selenols derived from monoterpenes Dedicated to Professor Jacek Gawronski on the occasion of his 70th birthday
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A convenient methodology for the synthesis of optically active selenols, derived from p-menthane, carane, and pinane, is described. The selenols were oxidized with air to give the optically active diselenides, and were also converted into the corresponding allylic selenides via reaction with Z- and E-cinnamyl, geranyl, and neryl chlorides. Oxidation of the allylic selenides with mCPBA gave the optically active alcohols via [2,3]-sigmatropic rearrangement of the in situ generated allylic selenoxides.
- Scianowski, Jacek,Rafalski, Jaroslaw,Banach, Anna,Czaplewska, Justyna,Komoszynska, Anna
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p. 1089 - 1096
(2013/10/08)
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- Metal-ligand core-shell nanocomposite catalysts for the selective semihydrogenation of alkynes
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Catalysts with a sheltered upbringing: Novel core-shell nanocomposite catalysts consisting of active metal nanoparticles encapsulated by macroligands have been prepared. They have Pd nanoparticles (PdNPs) as an active core and shell ligands having sulfoxide moieties coordinated to the PdNPs. The shell protects the catalyst from coordination by alkenes and allows the lead-free selective semihydrogenation of a wide range of alkynes without any additives (see scheme). Copyright
- Mitsudome, Takato,Takahashi, Yusuke,Ichikawa, Satoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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supporting information
p. 1481 - 1485
(2013/04/10)
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- Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis
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A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35°C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis.
- Oh, Ki-Hoon,Nguyen, Giang-Son,Kim, Eun-Young,Kourist, Robert,Bornscheuer, Uwe,Oh, Tae-Kwang,Yoon, Jung-Hoon
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experimental part
p. 67 - 73
(2012/09/07)
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- An efficient procedure for the 1,3-transposition of allylic alcohols based on lithium naphthalenide induced reductive elimination of epoxy mesylates
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An efficient protocol for the 1,3-transposition of allylic alcohols has been developed. The method is based on the pretransformation of allylic alcohols into the corresponding epoxy mesylates, followed by the reductive elimination of the resulting epoxy mesylates by using lithium naphthalenide (LN) as a reducing agent. Georg Thieme Verlag Stuttgart.
- Wu, Yen-Ku,Liu, Hsing-Jang,Zhu, Jia-Liang
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p. 621 - 623
(2008/12/22)
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- Total partial synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3- acetoxyocta-1,7-diene and (3S, 6S)-(-)-3,7-dimethylocta-1,7-diene-3,6-diol from geraniol
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The synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3-acetoxyocta-1,7- diene and (3S, 6S)-(-)3,7-dimethylocta-1,7-diene-3,6-diol via the rearrangement of the chiral 2,3-epoxy alcohol, with the system Ph3P, pyridine, I2 and H2O, is described.
- Liu, Zuosheng,Lan, Jiong,Li, Yulin,Xing, Yacheng,Cen, Wen
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p. 324 - 325
(2007/10/03)
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- Enzymatic alcoholysis of alkoxymethyl alkanoates: A possible approach for the kinetic resolution of tertiary alcohols
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The pivaloyloxymethyl and butanoyloxymethyl derivatives of tert-butanol and linalool (1.4) are readily accepted by hydrolases. Linalool derivative 4b is alcoholysed stereoselectively by Candida rugosa lipase (E=9.7).
- Franssen, Maurice C.R.,Goetheer, Earl L.V.,Jongejan, Hugo,De Groot, Aede
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p. 8345 - 8348
(2007/10/03)
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- Asymmetric [2,3]sigmatropic rearrangement of optically active allylic selenides
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Oxidation of an optically active allylic selenide derived from L-proline 1 with m-chloroperbenzoic acid afforded the corresponding chiral allylic alcohol 3 via asymmetric [2,3]sigmatropic rearrangement with fair enantioselectivity (up to 66% e.e.).
- Fujita, Ken-Ichi,Kanakubo, Mitsuhiro,Ushijima, Hirobumi,Oishi, Akihiro,Ikeda, Yoshikazu,Taguchi, Yoichi
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p. 987 - 988
(2007/10/03)
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- First synthesis of optically pure selenuranes and stereoselective alkaline hydrolysis. Their application to asymmetric [2,3] sigmatropic rearrangement of allylic selenoxides
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The first synthesis of optically pure selenuranes 1 has been accomplished by utilizing 2-exo-hydroxy-10 bornyl group as a chiral ligand Complete retention of the configuration has been observed in alkaline hydrolysis of 1 to give selenoxides 2. The structure of 1 and 2 has been fully established by X-ray crystallography. [2,3] Sigmatropic rearrangement of allylic selenoxides 2 gave the corresponding allylic alcohols 3 with up to 88% enantiomeric excess (ee). The [2,3] sigmatropic rearrangement of allylic selenoxides 2 progresses predominantly via an endo transition state.
- Kurose, Noriyuki,Takahashi, Tamiko,Koizumi, Toru
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p. 12115 - 12129
(2007/10/03)
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- First total synthesis of two new diglycosides, neohancosides A and B, from Cynanchum hancockianum
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Neohancosides A (1) and B (2) are monoterpene diglycosides isolated from Cynanchum hancockianum, which is a Chinese folk medicine having antitumor activity. First total synthesis of 1 and 2, (3R)-linaloyl and (3R)-8-hydroxylinaloyl 3-O-β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranosides were achieved stereoselectively using fluoride 12b as a glycosyl donor. The asymmetry of C-3 in 1 and 2 was introduced efficiently by separating diasteremers of (3R), (3S)-linaloyl and (3R), (3S)-8-benzoyloxylinaloyl 3-O-2,3,4-tri-O-benzoyl-β-D-glucopyranoside, 19 and 21 and 20 and 22, respectively. Absolute configurations of 1 and 2 were determined by enzymatic degradation of synthetic intermediates 33 and 34.
- Konda, Yaeko,Toida, Tsuneyuki,Kaji, Eisuke,Takeda, Kazuyoshi,Harigaya, Yoshihiro
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p. 123 - 143
(2007/10/03)
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- First total synthesis of new diglycosides, neohancoside A, and B from Cynanchum hancockianum
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First total synthesis of monoterpene diglycosides, neohancosides A (1) and B (2) from Cynanchum hancockianum were achieved stereoselectively using fluoride as a glycosyl donor. The absolute configurations of 1 and 2 were determined by enzymatic degradation of synthetic intermediates.
- Konda, Yaeko,Toida, Tsuneyuki,Kaji, Eisuke,Takeda, Kazuyoshi,Harigaya, Yoshihiro
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p. 4015 - 4018
(2007/10/03)
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- A Primeverosidase as a Main Glycosidase Concerned with the Alcoholic Aroma Formation in Tea Leaves.
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We isolated and characterized a primeverosidase from fresh tea leaves (Camellia sinensis var. sinensis cv.Yabukita) as a main glycosidase involved in alcoholic aroma (geraniol, linalool, benzyl alcohol, 2-phenylethanol, linalool oxides etc.) formation from their aroma precursors (β-primeverosides: 6-O-β-D-xylopyranosyl-β-D-glucopyranosides) in tea leaves.
- Guo, Wenfei,Yamauchi, Kazuyo,Watanabe, Naoharu,Usui, Taiichi,Luo, Shaojun,Sakata, Kanzo
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p. 962 - 964
(2007/10/02)
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- Synthesis of - and -Bisferrocenyl> Diselenides and Their Application to Asymmetric Selenoxide Elimination and Sigmatropic Rearrangement
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Novel optically-active bisferrocenyl> diselenides ( and ), each of which possesses two axial and two central elements of chirality, have been prepared by lithiation of commercially available chiral ferrocenes, followed by reaction with elemental selenium and air oxidation, in 77-80percent isolated yields.The structure of the -bisferrocenyl diselenide has been fully characterized by X-ray crystallography.Six chiral ferrocenyl vinylic selenides and six chiral allylic ferrocenyl selenides have been newly prepared by reaction of the diselenides with the corresponding propiolate derivatives and allylic halides.The oxidation of the vinylic selenides with m-chloroperbenzoic acid in various organic solvents produces axially chiral allenecarboxylic esters via asymmetric selenoxide elimination in 27-59percent chemical yields with high enantioselectivities (up to 89percent ee).Similar treatment of the allylic selenides afforded the corresponding chiral allylic alcohols via asymmetric sigmatropic rearrangement in 28-82percent chemical yields with high enantioselectivities (up to 89percent ee).The observed high enantioselectivities indicate that oxidation proceeds diastereoselectively, that the resultant chiral selenoxides are slow to racemize, and also that selenoxide elimination and sigmatropic rearrangement proceed with little loss of optical activity.
- Nishibayashi, Yoshiaki,Singh, Jai Deo,Fukuzawa, Shin-ichi,Uemura, Sakae
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p. 4114 - 4120
(2007/10/02)
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- A catlaytic tellurium process for the transposition of allylic hydroxyl groups and carbon-carbon double bonds
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As little as 0.1 molar equivalent of elemental tellurium in combination with excess (up to 3 molar equivalents) reducing agent (HOCH2SO2Na·H2O, NaBH4, or LiEt3BH) effects the telluride-ion mediated transposition of allylic hydroxyl groups and carbon-carbon double bonds that proceeds via the epoxy tosylate. The workup is much more convenient than when a molar equivalent of tellurium is used.
- Kumar, Archana,Dittmer, Donald C.
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p. 5583 - 5586
(2007/10/02)
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- An extremely mild desulfurization of thiiranes: An efficient transformation from geraniol to (+)- and (-)-linalool
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Thiirane was transformed to alkene very efficiently at -78°C by triethylborane initiated radical reaction with tributyltin hydride. Enantiomerically pure (+)- and (-)-linalools were derived from geraniol in four steps including the alkene formation reaction.
- Uenishi,Kubo
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p. 6697 - 6700
(2007/10/02)
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- A Tellurium Transposition Route to Allylic Alcohols: Overcoming Some Limitations of the Sharpless-Katsuki Asymmetric Epoxidation
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Good yields of enantiomeric allylic alcohols can be obtained in high enantiomeric excess (ee) by combining Sharpless-Katsuki asymmetric epoxidation process (SAE) with tellurium chemistry.The advantages of the tellurium process are as follows: (1) the 50percent yield limitation on the allylic alcohol in the Sharpless kinetic resolution (SKR) can be overcome; (2) allylic tertiary alcohols which are unsatisfactory substrates in the SKR can be obtained in high optical purity; (3) optically active secondary allylic alcohols with tertiary alkyl substituents (e.g. tert-butyl) at C-1 can be obtained in high ee; (4) optically active sterically congested cis secondary alcohols can be obtained in high ee; and (5) the nuisance of the slow SAE of some vinyl carbinols can be avoided.The key step in the reaction sequence is either a stereospecific 1,3-transposition of double bond and alcohol functionalities or an inversion of the alcohol configuration with concomitant deoxygenation of the epoxide function in epoxy alcohols.Trans secondary allylic alcohols can be converted to cis secondary allylic alcohols by way of erythro epoxy alcohols (glycidols); threo glycidyl derivatives are converted to trans secondary allylic alcohols.These transformations are accomplished by the action of telluride ion, generated in situ from the element, on a glycidyl sulfonate ester.Reduction of elemental Te is conveniently done with rongalite (HOCH2SO2Na) in an aqueous medium.This method is satisfactory when Te2- is required to attack at primary carbon site of a glycidyl sulfonate.In cases where Te2- is required to attack a secondary carbon site, reduction of the tellurium must be done with NaBH4 or LiEt3BH.Elemental tellurium is precipitated during the course of the reactions and can be recovered and reused.
- Dittmer, Donald C.,Discordia, Robert P.,Zhang, Yanzhi,Murphy, Christopher K.,Kumar, Archana,et al.
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p. 718 - 731
(2007/10/02)
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- Larger Scale Preparation of Optically-active Allylic Alcohols
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An efficient and practical synthesis of optically-active allylic alcohols from 2,3-epoxytoluene-p-sulfonates by the in situ formation of the epoxy iodides and their subsequent reduction with zinc-copper couple has been established.Application of this procedure to the larger-scale synthesis of (S)-(+)-but-3-en-2-ol from (2S,3S)-3-methylglycidyl toluene-p-sulfonate has also been investigated.
- Balmer, Ethnie,Germain, Andrew,Jackson, William P.,Lygo, Barry
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p. 399 - 400
(2007/10/02)
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- Oxirane Ring-Opening with Alcohol Catalyzed by Organotin Phosphate Condensates. Complete Inversion at Tertiary and Benzylic Centers
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Regio- and stereospecific ring-opening of chiral oxiranes has been effected by organotin phosphate condensates catalyst.Alcohols attack on the tertiary and benzylic positions exclusively.Despite seemingly acidic character of the catalyst in terms of regioselectivity the chiral centers are completely inverted.The new methodology is applied to synthesis of enantiomerically pure linalool and to conversion of commercially available (R)-styrene oxide into the (S)-counterpart.
- Otera, Junzo,Niibo, Yoshihisa,Nozaki, Hitosi
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p. 7625 - 7634
(2007/10/02)
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- Asymmetric Induction in the Oxidation of Paracyclophane-Substituted Selenides. Application of Chirality Transfer in the Selenoxide Sigmatropic Rearrangement
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When selenides derived from paracyclophane systems were oxidized, the chiral aryl substituent provided for asymmetric induction to the new selenoxide chiral center.The ratio of diastereomeric selenoxides obtained depended upon whether the oxidation was performed under kinetic conditions or whether the selenoxides were allowed to equilibrate.Thus 4-(methylseleno)paracyclophane (10) gave a 1:1 kinetic ratio of selenoxides 11 and 12 on oxidation with m-chloroperbenzoic acid and a 30:1 ratio at equilibrium (thermodynamic ratio).The more hindered 4-(methylseleno)-15-(p-toluenesulfonyl)paracyclophane (23) was prepared in almost optically pure form.It gave a better kinetic ratio of selenoxides 24 and 25 (4.5:1) but a poorer thermodynamic one (1.5:1).The relative configuration of 11 and 12 and the absolute configuration of 24 and 25 were assigned.A geranyl selenide substituted with a resolved paracyclophane substituent was oxidized and allowed to undergo a selenoxide sigmatropic rearrangement to linalool.This sequence proves that the sigmatropic rearrangement of γ,γ-dialkylallyl selenoxides proceeds through an endo transition state and illustrates the use of asymmetric induction during oxidation followed by chirality transfer by rearrangement to prepare optically active allylic alcohols.
- Reich, Hans J.,Yelm, Kenneth E.
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p. 5672 - 5679
(2007/10/02)
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- Telluride-mediated stereospecific conversion of racemic E-allylic alcohols to homochiral Z-allylic alcohols; transposition of primary and secondary allylic alcohols via glycidol derivatives
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Racemic trans-secondary allylic alcohols can be converted to homochiral cis-secondary allylic alcohols by means of a telluride-mediated transposition reaction applied to the homochiral glycidol obtained from a Sharpless kinetic resolution. (+)-Linalool is obtained in>95% enantiomeric excess from geraniol, an example of a transposition of a primary allylic alcohol to a homochiral tertiary alcohol.
- Discordia, Robert P.,Murphy, Christopher K.,Dittmer, Donald C.
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p. 5603 - 5606
(2007/10/02)
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- Isomerizations of Citronellal to Isopulegol and Geraniol to Linalool Catalyzed by Solid Acids and Bases
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Citronellal was isomerized to isopulegol over SiO2-Al2O3, TiO2,-ZrO2, FeSO4, NiSO4, Ti(SO4)2, Zr(SO4)2 and Al2O3, with the selectivity higher than 91percent.Geraniol was also isomerized mainly to linalool over SiO2-Al2O3 and those four metal sulfates, and the selectivity on SiO2-Al2O3 and FeSO4 was higher than 81percent.
- Arata, Kazushi,Matsuura, Chiharu
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p. 1797 - 1798
(2007/10/02)
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- TERPENIC GLYCOSIDES FROM PLUCHEA INDICA
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Investigation of the aerial parts of Pluchea indica afforded five new terpenic glycosides, linalyl glucoside, linalyl apiosyl glucoside, 9-hydroxylinalyl glucoside, plucheosides A and B, in addition to 15 known compounds.The structures of new compounds were elucidated on the basis of chemical and spectral data.Key Word Index - Pluchea indica; Compositae; monoterpene glycoside; sesquiterpene glycoside; ionone derivative glycoside; lignan.
- Uchiyama, Taketo,Miyase, Toshio,Ueno, Akira,Usmanghani, Khan
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p. 3369 - 3372
(2007/10/02)
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- Chemische und Chemotaxonimische Untersuchungen der Pterophyten. LXII. Chemische Untersuchungen der Inhaltsstoffe von Arachniodes maximowiczii OHWI
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Two new ent-rosane norditerpenes, ar-maximic acid (I) and ar-maximol (II), were isolated from the fronds of Arachniodes maximowiczii OHWI, and were shown to have the structures of 2-hydroxy-19-nor-ent-rosa-1,3,5(10),15(16)-tetraene 18-oic acid (I) and 2,18-dihydroxy-19-nor-ent-rosa-1,3,5(10),15(16)-tetraene (II) by chemical, spectroscopic and X-ray crystallographic methods.In addition, six glycosides of acyclic terpenes were isolated, and their structures were elucidated as 3(S)-linalool O-β-D-glucopyranoside (III), 3(S)-linalool O-β-D-(6'-O-β-L-fucopyranosyl)glucopyranoside (IV), 13-hydroxygeranyllinalool 13-O-β-D-(6'-O-β-L-fucopyranosyl)glucopyranoside (V), 13-hydroxygeranyllinalool 3,13-O-β-D-diglucopyranoside (VI), 13-methoxygeranyllinalool O-β-D-glucopyranoside (VII) and 15-methoxy-3,7,11,15-tetramethylhexadeca-1,6(E),10(E),13(E)-tetraene O-β-D-glucopyranoside (VIII), mainly by spectroscopic methods.Compounds VII and VIII, obtained as an inseparable mixture may be artefacts.Maltol and maltol β-D-glucoside were also isolated.Keywords - Arachniodes maximowiczii; ent-rosane-type norditerpene; acyclic monoterpene glycoside; acyclic diterpene glycoside; Aspidiaceae; fern; chemotaxonomy; X-ray analysis; 13C-NMR
- Tanaka, Nobutoshi,Sakai, Hideko,Murakami, Takao,Saiki, Yasuhisa,Chen, Chiu-Ming,Iitaka, Yoichi
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p. 1015 - 1022
(2007/10/02)
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