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1.
P. F. Vlad D. P. Popa E. C. Gorincioi M. N. Coltsa G. N. Mironov 《Russian Chemical Bulletin》2000,49(1):98-101
A synthetic route to 11-hydroxydrim-8(9)-en-7-one and 11,12-hydroxydrim-8(9)-en-7-one, valuable key intermediates for the
preparation of naturally occurring biologically active drimanic sesquiterpenoids, starting from easily available drim-8(9)-en-7-one
was developed. 11-Hydroxydrim-8(9)-en-7-one was obtained by peracidic oxidation of the enol acetate of drim-8(9)-en-7-one.
11,12-Dihydroxydrim-8(9)-en-7-one was synthesized from drim-8(9)-en-7-one by two routes, namely, by a five-step procedurevia 11-hydroxydrim-8(9)-en-7-one and by bromination of drim-8(9)-en-7-one with NBS to give 11,12-dibromodrim-8(9)-en-7-one followed
by its acetoxylation and deacetylation.
Deceased
Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 95–98, January, 2000. 相似文献
2.
Alexandru Ciocarlan Carolina Edu Andrei Biriiac Lidia Lungu Aculina Aricu Michele D'Ambrosio 《合成通讯》2013,43(22):3020-3033
A series of 15 new polyfunctional drimanic compounds have been obtained by synthesis via dye-sensitized photooxygenation, bromination with N-bromosuccinimide, and electrochemical transformation of drim-7,9(11)-diene 1 and drim-8-en-7-one 2. Three alternative syntheses of 12-acetoxy-drim-7,9(11)-diene 8 and two of 11-bromo-drim-8(9)-en-7-one 10 have been accomplished. For the first time a drimanic compound 12 with an aromatic ring B has been synthesized and the experimental conditions for the selective bromination at C11 and C12 methyl groups of drim-8-en-7-one 2 have been optimized. The synthesized compounds are suitable intermediates for the preparation of natural drimane-type compounds and some of them have shown good antimicrobial and antifungal activities. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.] 相似文献
3.
The natural drimane sesquiterpenoid lactone 5,6-dehydro-7-oxoisodrimenin was synthesized from drim-8-en-7-one as well as from 7-oxoisodrimenin. 相似文献
4.
P. F. Vlad M. N. Coltsa A. N. Aricu A. G. Ciocarlan E. C. Gorincioi C. G. Edu C. Deleanu 《Russian Chemical Bulletin》2006,55(4):703-707
An efficient two-step procedure for photooxidative dehydrogenation of drimane and 11-homodrimane compounds containing an 8-en-7-one
structural unit into α,α′-dienones was elaborated. The method is based on the transformation of ketones into the respective
enol acetates followed by photosensitized oxygenation. Methyl 7-oxo-11-homodrima-5,8-dien-12-oate, 5,6-dehydro-7-ketoisodrimenine,
11-acetoxydrima-5,8-dien-7-one and 11,12-diacetoxydrima-5,8-dien-7-one were prepared in high yields starting from methyl 7-oxo-11-homodrim-8-en-12-oate,
7-oxoisodrimenine, 11-hydroxydrim-8-en-7-one and 11,12-diacetoxydrim-8-en-7-one, respectively.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 678–682, April, 2006. 相似文献
5.
M. N. Koltsa G. N. Mironov S. T. Malinovskii P. F. Vlad 《Russian Chemical Bulletin》1996,45(1):208-214
A method was elaborated for the synthesis of polyfunctional compoonds of the drimane series,viz., drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives, potential intermediates for the synthesis of natural biologically active drimane sesquiterpenoids starting from norambreinolide. The key intermediate of the above drimane compounds is methyl 7-oco-11-homodrim-8(9)-en-12-oate, prepared by electrochemical oxidation of a mixture of isomeric methyl bicyclohomofarnesenoates obtained from norambreinolide.Institutul de Chimie, Academia de Stiinte Republica Moldova, 3 str. Academiei, 277028 Chisinäu, Republica MoldovaTranslated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 216–222, January, 1996. 相似文献
6.
K. I. Kuchkova A. N. Aryku I. P. Dragalin P. F. Vlad 《Chemistry of Natural Compounds》2005,41(2):190-193
Drim-9(11)-en-8α-ol and drim-9(11)-en-8β-ol were synthesized in six steps from drimenol. Drimenol was oxidized by P2O5 and DMSO to drimenal, which isomerized with p-TsOH into isodrimenal. Isodrimenal was reduced by NaBH4 into isodrimenol, epoxidation of which by m-CPBA gave a mixture (3.4:1) of α- and β-epoxyisodrimenols. These reacted with tosyl chloride in Py to give a mixture of α- and β-epoxyisodrimenol tosylates. Treatment of the tosylate mixture with KI and then Ph3P produced a mixture of drim-9(11)-en-8α- and -8β-ols that was separated chromatographically. The overall yield was ∼26%.__________Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 152–155, March–April, 2005. 相似文献
7.
A naturally occurring drimanic sesquiterpenic lactone, isodrimenin, was synthesized from drim-8-en-7-one (1). Compound1 was converted to the known 11,12-dihydroxydrim-8-en-7-one, which was oxidized with PCC to give 7-oxoisodrimenin. The thioketal of the latter compound was reduced with nickel boride or Raney nickel to give the target isodrimenin. 相似文献
8.
Pavel F. Vlad Alexandru G. Ciocarlan Mihai N. Coltsa Alexandr V. Baranovsky Natalya B. Khripach 《合成通讯》2013,43(22):3960-3972
This article describes a new efficient synthesis of drim-7,9(11)-diene and its hydroxylated derivates from drim-8-en-7-one. Reduction of this ketone with NaBO4 in the presence of CeCl3 · 7H2O afforded regio- and stereoselectively drim-8-en-7β-ol in a high yield. Its dehydration with H2SO4 under mild conditions led to drim-7,9(11)-diene. Noncatalytic oxidation of drim-7,9(11)-diene with OsO4 and the catalytic oxidation with the pair OsO4–NMO gave, in a high yield, depending on conditions, driman-7β,8β,9α,11-tetraol or its mixture with drim-7-en-9α,11-diol and drim-9(11)-en-7α,8α-diol. Under optimal conditions the total yield of these diols reached 89%. The separate, noncatalytic oxidation of drim-7-en-9α,11-diol and of drim-9(11)-en-7α,8α-diol with OsO4 afforded driman-7α,8α,9α,11-tetraol. 相似文献
9.
An efficient one-step synthesis of the diacetate of the tetracyclic triterpenoid onoceranediol (4) by radical cleavage of the readily available 12-hydroperoxy-8α,12-epoxy-11-bishomodrimane is described. Drim-9(11)-en-8α-yl
acetate (7) is formed in this reaction as a byproduct. Onoceranediol diacetate 4 is converted into onoceranediol on treatment with LiAlH4, and acetate 7 is transformed into drim-9(11)-en-8α-ol on saponification.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2571–2573, November, 2005. 相似文献
10.
Pavel Vlad Elena Gorincioi Aculina Aricu Alic Barba Ada Manzocchi Enzo Santaniello 《Tetrahedron: Asymmetry》2010,21(17):2108-2116
The asymmetric dihydroxylation of drim-7-en-11-ol was studied in detail and diastereomerically pure driman-7α,8α,11- and driman-7β,8β,11-triols were prepared. Further elaboration of driman-7α,8α,11-triol afforded 14,15-bisnorlabd-7α,8α-isopropylidenedioxy-11,13-dione from which a novel chlorinated bisnorlabdanic compound (14,15-bisnorlabd-12-ene-12-chloro-8α,13-epoxy-7α-ol-11-one) and an unusual dichloro-derivative, 13,14,15,16-tetranorlabd-12-dichloro-7α-acetoxy-8α-ol-11-one, were obtained. 相似文献
11.
A. A. Panasenko E. C. Gorincioi A. N. Aricu E. A. Barcari K. Deleanu P. F. Vlad 《Russian Chemical Bulletin》2004,53(12):2700-2705
One- and two-dimensional homo- and heteronuclear correlation proton, carbon, proton—proton, and proton—carbon NMR spectra of fifteen drimanic sesquiterpenoids: 11,12-dibromodrima-5,8-dien-7-one, drim-8-en-7-one, 11-hydroxydrim-8-en-7-one, 11,12-dihydroxydrim-8-en-7-one, 11-hydroxy-11,12-epoxydrim-8-en-7-one, 11-hydroxy-11,12-epoxydrim-8-en-7-one, 8,9-epoxydriman-7-one, 8,9-epoxydriman-7-ol, 11,12-diacetoxydrim-8-en-7-ol, drimane-7,8,11-triol, 7,8-isopropylidenedioxydriman-11-al, 9, 11-dihydroxydrim-7-en-6-one, drimane-7,8,9-triol, drimane-7,8,11-triol, and drim-8-ene-7,11,12-triol were studied. The proton and carbon chemical shifts were assigned.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2589–2594, December, 2004. 相似文献
12.
New Ambra Odorants by Photoreactions of 15, 16-Dinorlabd-8(20)-en-13-one . UV.-irradiation of 15,16-dinorlabd-8(20)-en-13-one ( 1 ) led to the fragmentation product 4 and its photo-cyclisation product 5 . Ethers 6 and 7 and the βγ-unsaturated alcohols 8 and 10 were formed via ketone 9 , a double bond isomer of 1 . The olfactory properties of the photo-products are described. 相似文献
13.
K. I. Kuchkova A. N. Aryku A. N. Barba P. F. Vlad Ya. Lipkovskii Yu. A. Simonov V. Kh. Kravtsov 《Chemistry of Natural Compounds》2011,47(2):223-228
Products from the reaction of 11-dihomodriman-8α-ol-12-one with several reagents such as MeSO3SiMe3, CF3SO3SiMe3, Sc(CF3SO3)3, conc. H2SO4 in EtOH (30% solution), and Amberlist-15 ion-exchange resin were studied. 11-Dihomodrim-8(9)-en-12-one and its oxime were
synthesized. The reaction of its oxime with H3PO4 (86%) or CF3CO2H produced (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydro-1H-naphtho [1,2-e]-3-methyl-4,5-dihydro-[1,2,6]-oxazine; with p-TsCl in Py, (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydro-1H-naphtho[1,2-d]-2-methylpyrroline-N-oxide; and with PCl5 in Et2O, 11-acetylaminodrim-8(9)-ene and 11-methylaminooxodrim-8(9)-ene. 相似文献
14.
Shubhangi C. Joshi Kunjbihari N. Trivedi 《Monatshefte für Chemie / Chemical Monthly》1992,123(6-7):557-564
Summary The Claisen rearrangement of 7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 a) gave 7-hydroxy-8-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (3 a) and 2,3-dihydro-2,6-diphenyl-3-methyl-(7H)furo[2,3-h]-1-benzopyran-7-one (7 a). 2-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 b) afforded4 b and7 b. 8-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (12) gave only the alkali soluble product 7-hydroxy-8-methyl-6-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (13).3 a,4 b, and13 were further cyclized in acidic medium to9 a,10 b, and14 followed by dehydrogenation.This paper is dedicated to Dr. F. M. Dean, Department of Organic Chemistry, Robert Robinson Laboratories, University of Liverpool, Liverpool, U. K., on his retirement 相似文献
15.
A method for preparative production of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1), a glycoside from Panax japonicus, chikusetsusaponin-LT8 was developed. Chemical transformation of betulafolientriol, a component of Betula leaves extract, produced the 12-keto-20S-protopanaxadiol (3β,20S-dihydroxydammar-24-en-12-one) (2), exhaustive glycosylation of which by 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide (3) under Koenigs—Knorr reaction conditions with subsequent removal of protecting groups formed 3β,20S-dihydroxydammar-24-en-12-one
3,20-di-O-β-D-glucopyranoside (1). The principal glycosylation product was 3β,20S-dihydroxydammar-24-en-12-one 3-O-β-D-glucopyranoside if equimolar amounts of (2) and (3) were used.
__________
Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–48, January–February, 2006. 相似文献
16.
7-endo-t-Butyldimethylsilyloxybicyclo[3.3.0]oct-8-en-2-one (7) is an important key intermediate for the synthesis of pharmacologically interesting prostacyclin analogs, 9(0)-methanoprostacyclin2 and 9(0)-methano-Δ6-PGI1.3 In addition it seems to be a valuable synthetic intermediate for the total synthesis of antitumor sesquiterpenoid coriolin family.4 相似文献
17.
L. A. Baeva A. D. Ulendeeva A. A. Fatykhov N. K. Lyapina 《Russian Journal of Organic Chemistry》2010,46(7):1066-1069
The reduction of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo[3.3.1]non-7-en-6-one with aluminum hydride, lithium tetrahydridoaluminate,
or lithium tris(tert-butoxy)hydridoaluminate in tetrahydrofuran gave 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo[3.3.1]non-7-en-6-ol. 8-Methyl-5-methylsulfanylmethyl-3-thiabicyclo[3.3.1]nonan-6-ol
was obtained by reduction of the title compound with sodium tetrahydridoborate in pyridine or dimethylformamide. The reaction
of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo[3.3.1]non-7-en-6-one with hydroxylamine hydrochloride afforded the corresponding
oxime. 相似文献
18.
Frederick Kurzer Jayantilal N. Patel 《Monatshefte für Chemie / Chemical Monthly》1984,115(6-7):809-823
8-Bromo-1-carboxydiisophor-2(7)-en-3-one is obtainable from diisophorone by successive monobromination andKoch-Haaf carboxylation, performed in either sequence. Nucleophilic replacement of its 8-bromo-substituent by acetolysis or methanolysis occurs with simultaneous migration, resulting in the 4-acetoxy- or 4-methoxy-compounds, respectively. In contrast, alkaline hydrolysis yields the 8-hydroxy-compound as main-product; this serves as the precursor of 3,8-diketodiisophor-2(7)-ene-1-carboxylic acid. The configuration of the 4- and 8-substituents is tentatively assigned on the basis of i.r. spectral data.
Diisophoron und verwandte Verbindungen, 13. Mitt.: Nucleophile Reaktionen von 8-Bromdiisophoron-1-carbonsäure
Zusammenfassung 8-Brom-1-carboxydiisophor-2(7)-en-3-on ist aus Diisophoron durch Monobromierung undKoch-Haaf-Carboxylierung zugänglich; die Reaktionen sind in beliebiger Reihenfolge ausführbar. Nucleophiler Austausch des 8-Brom-Substituenten durch Acetolyse und Methanolyse erfolgt unter gleichzeitiger Isomerisierung, wobei 4-Acetoxy- oder Methoxy-Verbindungen entstehen. Im Gegensatz dazu liefert alkalische Hydrolyse hauptsächlich die 8-Hydroxyl-Verbindung; diese dient als Ausgangsmaterial für die Darstellung der 3,8-Diketodiisophor-2(7)-en-1-carbonsäure. Vorläufige Konfigurationen der 4- und 8-Substituenten werden auf Grund von IR-Spektren vorgeschlagen.相似文献
19.
Géraldine Le Goff Emilie Adelin Guillaume Arcile Jamal Ouazzani 《Tetrahedron letters》2017,58(24):2337-2339
The first total synthesis of (±)-EA-2801, a naturally occurring 4-hydroxycyclopent-2-en-1-one acrylate produced by the fungus Trichoderma atroviridae UB-LMA, was achieved The synthesis started from furfuryl alcohol, manufactured industrially from furfural, produced from waste biomass such as corncobs or sugar cane bagasse. (±)-EA-2801 was synthesized in 5 steps and 71% overall yield starting from 4-hydroxycyclopent-2-en-1-one. Enantio-pure (R)- and (S)-EA-2801 were obtained from racemic mixture by preparative chiral supercritical fluid chromatography (SFC). 相似文献
20.
Treatment of geranylacetone with NaNO2 in AcOH affords 6,10-dimethyl-9-nitroundeca-5E,10-dien-2-one as the major product. This product was used to synthesize 6,10-dimethyl-9-methyleneundec-5E-en-2-one, a component of the essential oil from the roots of theSaussurea lappa plant.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1299–1302, July, 1999. 相似文献