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1.
A synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate () and propionate () is described. (2S)-2-Methyldecan-1-yl lithium () was reacted with (3S,4S)-3,4-dimethyl-γ-butyrolactone () to yield the ketoalcohol which upon Huang-Minlon reduction furnished (2S,3S,7S)-3,7-dimethylpentadecan-2-ol (). Acylations gave the esters and . The (2S)-2-methyldecan-1-yl lithium was obtained via asymmetric synthesis. The chiral lactone was obtained from (2S,3S)-trans-2,3-epoxybutane and dimethyl malonate. 相似文献
2.
Jack E. Baldwin Robert M. Adlington Bernard J. Rawlings Richard H. Jones 《Tetrahedron letters》1985,26(4):485-488
Practical procedures for the resolution of racemic modification of (1, 2)-and (1, 2)-1-amino-2-ethylcyclopropane-1-carboxylic acid ,,(1, 2)- and (1, 2)-1-amino-2-methylcyclopropane-1-carboxylic acid ,, and (1, 2)- and (1, 2)-1-amino-2-methylcyclopropane-1-carboxylic acid , are described; the structures as ,, and were confirmed by X-ray-crystallographic methods. 相似文献
3.
James D. Morrison Edward R. Grandbois Sachiko I. Howard Gary R. Weisman 《Tetrahedron letters》1981,22(28):2619-2622
Four chiral aminodiols from ring opening of ()-propylene oxide and ethylene oxide wiht n-butylamine and () or ()-α-methylbenzylamine were used to modify LiAlH4. Assymetric reduction of acetophenone and propiophenone gave the highest percent enantiomeric excess when the modifier was made from ()-oxide and ()-amine. 相似文献
4.
(1,5)-(-)-Karahana ether (8,8-dimethyl-2-methylene-6-oxabi-cyclo[ 3.2.1]octane) and (1,5)-(-)-karahana lactone (8,8-dimethyl-2-methylene-6-oxabicyclo [3.2.1]octan-7-one) were synthesized from ()-3-hydroxy-2,2-dimethylcyclo-hexanone. The natural karahana lactone was shown to be almost racemic (. 1.3 % e.e.). 相似文献
5.
By appropriate choice of reaction conditions, the enantiomerically pure ()-(+)-2-(-tolylsulfinyl)cycloalkenone can be converted into an ()-or an ()-3-substituted cycloalkanone in good to excellent enantiomeric purity. 相似文献
6.
Positive n → π* Cotton effects were shown by (-2-deuteriopropionic acid, ()-2-deuteriosuccinic acid, ()-2-deuterioglycine and ()-2-deuterioglycolic acid. Using an octant projection and conformational and chiroptical data, it can be shown that the deuterium substituent makes a dissignate contribution to the Cotton effect. 相似文献
7.
Such an asymmetric [2,3]-Wittig variant that is both highly enantio- and erythro-selective is described within the context of the chiral synthesis of the insect pheromones, (3, 4)-4-methyl-3-heptanol and ()-4-methyl-3-heptanone. 相似文献
8.
The Sharpless asymmetric epoxidation was used for the synthesis of D--dihydrosphingosine triacetate and (2, 3, 5)-2-acetamino-5,9-dimethyl-8-decene-1,3-diol, whose 13C-NMR study coupled with biogenetic consideration enabled us to propose (2, 3, 5,13, 14)-stereochemistry for aplidiasphingosine. 相似文献
9.
Asymmetric cyclizations of methyl (E)-3-oxo-9-phenoxy-7-nonenoate () or methyl (E)-3-oxo-9-(methoxycarbonyl)oxy-7-nonenoate () without added base were carried out in the presence of a catalytic amount of palladium(II) acetate and chiral diphosphine as ligands. Allylic carbonate reacted by use of Pd(OAC)2-(S)-(R)-BPPFA at room temperature to give (R)-3-vinylcyclohexanone (), after decarboxylation, in up to 48% e. e. 相似文献
10.
《Tetrahedron》1986,42(16):4413-4420
(2,3,1')-Stegobinone [2,3-dihydro-2,3,5-trimethyl-6-(1'-methyl-2'-oxobutyl)-4H-pyran-4-one], the pheromone of L., was synthesized with stereocontrol at C-2 and C-1' starting from ethyl ()-3-hydroxybutanoate and methyl ()-3-hydroxy-2-methylpropanoate. The dihydro-γ-pyrone ring of the pheromone was constructed by an intramolecular acylation followed by acid-catalyzed cyclization. 相似文献
11.
Titanium(IV) chloride-mediated reaction of 4,5-dihydro-2-(trimethylsiloxy)-3-(trimethylsilyl)furan (1a) with acetaldehyde gave (3S*, 1′R*)-4,5-dihydro-3-(1′hydroxyethyl)-3-(trimethylsilyl)-2(3)furanone (2a), which afforded selectively either (Z)- or (E)-α-ethylidene-γ-butyrolactone (3a) under proper conditions. Facile isomerization of 2a into (3S*, 1′R*)-4,5-dihydro-3-&{1′-(trimethylsiloxy)ethyl}-2(3)furanone (4) suggests an intriguing stereochemical outcome from 2a to (E)-3a via an enolate of 4. 相似文献
12.
Lithiation of both ()- and ()-3-trimethylsilyl-2-propenyl ,-diisopropyl carbamate 2 affords the (2) -lithium compound 3. Aluminium- or titanium-mediated addition to aldehydes, 4 gives (1)-(3*4*)-enol carbamates 7. A stereospecific Peterson elimination (borontriflouride- or base-mediated) introduces the second double bond either with (3)- or with (3)-configuration. So just by reagent selection for each of the two steps, (1,3)-, (1,3)-, (1,3)-, or (1,3)- dienes 8 - 11, respectively, are prepared with stereoselectivities up to > 99.7% 相似文献
13.
(3,6)-(?)-3-Hydroxy-1,7-dioxaspiro[5.5]undecane 3a and its antipode were synthesized from ()-malic acid. 相似文献
14.
()-5-Hydroxy-6--8,11,14--eicosatetraenoic acid (5-HETE) (1) and its enantiomer are readily available by a chemical synthesis from arachidonic acid which includes a chromatographic separation of diastereomeric urethanes (3) made from (±)-5-HETE methyl ester and the isocyanate 4 derived from dehydroabietylamine. 相似文献
15.
Stereospecific conversion of β-hydroxyallylglycine derivatives into (2, 3, 4) 1 and (2, 3, 4) 2 halo- or mercuri-lactonization has been described. 相似文献
16.
Combination of ()-4--butyldimethylsiloxy-2-cyclopentenone, ()-()-3--butyldimethylsiloxy-1-iodo-1-octene, and 6-methoxycarbonyl-2-hexynal via the tandem organo-copper conjugate addition—aldol reaction procedure leads directly to a 5,6-dehydroprostaglandin E2 derivative, which can be transformed to a variety of chiral primary prostaglandins in a stereoselective manner. 相似文献
17.
HPLC-fractionated (p)- and (p)-phosphoramidites underwent tetrazole-catalyzed coupling to support-bound nucleosides to give intermediary phosphates with epimerization at phosphorus, as shown by conversion to epimerized mixtures of dinucleoside phosphorothioates. 相似文献
18.
Halogen cleavage reactions of -(-PhCHDCHD)Mn(CO)4, PEt3 () are studied in detail and are found to proceed either predominantly with retention or inversion, or non-stereospecifically, depending on reaction conditions. Reaction mechanisms involving SE2 (inversion), SE2 (retention) and SE (oxidative) processes are proposed, demonstrating that halogen cleavage reactions of straddle the mechanistic borderline between electrophilic substitution and oxidation processes of transition metal alkyl compounds. 相似文献
19.
Masatoshi Asami 《Tetrahedron letters》1985,26(47):5803-5806
cis-4-t-Butyldimethylsiloxy-2-cyclopenten-1-ol and cis-4-tetrahydropyranyloxy-2-cyclopenten-1-ol were obtained with high enantiomeric excesses (ee) by the reaction of cis-3,4-epoxycyclopentan-1-ol derivatives with chiral lithium amide. An application to the syntheses of both ()- and ()-4-hydroxy-2-cyclopentenone was demonstrated. 相似文献
20.
The aldol reaction of formaldehyde with the dicyclopentylborinyl enolate derived from -(or -) 1-tert-butyldimethylsilyloxy-l-cyclohexylbutan-2-one, followed by desilylation and sodium meta-periodate oxidation, provides -(or -) β-hydroxyisobutyric acid. 相似文献