Synthesis of (±)-8-deisopropyladunctin B.

Abstract:

:(±)-8-Deisopropyladunctin B, the deisopropyl form of adunctin B, which was isolated from the leaves of Piper aduncum (Piperaceae) collected in Papua New Guinea, was synthesized in 0.77% overall yield in 17 steps from 5,7-dimethoxycoumarin-3-carboxylate. The key step was our original stereoconvergent skeleton transformation from 1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-one to 1,2,4a,9b-tetrahydrodibenzofuran-4-ol with dimethylsulfoxonium methylide.

authors

Nomura S,Arimitsu K,Yamaguchi S,Kosuga Y,Kakimoto Y,Komai T,Hasegawa K,Nakanishi A,Miyoshi T,Iwasaki H,Ozeki M,Kawasaki I,Kurume A,Ohta S,Yamashita M

doi

10.1248/cpb.60.94

subject

Has Abstract

pub_date

2012-01-01 00:00:00

pages

94-103

issue

1

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/60.94

journal_volume

60

pub_type

杂志文章
  • Hydnellins A and B, nitrogen-containing Terphenyls from the mushrooms Hydnellum suaveolens and Hydnellum geogerirum.

    abstract::Fractionation of methanol extracts of the fruit bodies of two inedible mushrooms Hydnellum suaveolens and Hydnellum geogerirum (Thelephoraceae) resulted in isolation of two new p-terphenyl derivatives named hydnellins A and B and sarcodonin delta possessing N-oxide. Their structures were determined by 2D NMR, IR, UV s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.912

    authors: Hashimoto T,Quang DN,Kuratsune M,Asakawa Y

    更新日期:2006-06-01 00:00:00

  • A synthetic study on antiviral and antioxidative chromene derivative.

    abstract::An efficient synthesis of the antiviral and antioxidative chromene (1) was achieved. A small amount of chromene 1 could be derived from plastoquinones 2 and 3, the major constituents of the brown alga, Sargassum micracanthum. By the following synthetic scheme involving its application, many kinds of analogs can be syn...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.391

    authors: Mori J,Iwashima M,Takeuchi M,Saito H

    更新日期:2006-03-01 00:00:00

  • Inner-hydrogen tautomerism in some 5,15-unsymmetrically disubstituted and beta-unsubstituted porphyrins.

    abstract::5,15-Unsymmetrically disubstituted and beta-unsubstituted porphyrins such as 5-R, 15-(3,5-dimethoxyphenyl) porphyrins [where R=2-benzyloxy-1-naphthyl (1), 2-(2-naphthylmethoxy)-1-naphthyl (2), anthryl (3), or 2,4,6-triphenylphenyl (4)] and 5-(2-benzyloxy-1-naphthyl), 10,15,20-tri(3,5-dimethoxyphenyl) porphyrin (1') we...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1041

    authors: Tohara A,Sato M

    更新日期:2008-07-01 00:00:00

  • Density of hydroxyl radicals generated in an aqueous solution by irradiating carbon-ion beam.

    abstract::The density of hydroxyl radicals (·OH) produced in aqueous samples by exposure to X-ray or carbon-ion beams was investigated. The generation of ·OH was detected by the electron paramagnetic resonance (EPR) spin-trapping technique using 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) as the spin-trapping agent. When the concen...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c14-00736

    authors: Matsumoto K,Ueno M,Nakanishi I,Anzai K

    更新日期:2015-01-01 00:00:00

  • A new synthesis of indoloquinolizines by Pictet-Spengler reaction of tryptamine type 1,2-dihydropyridines utilizing sec-nitrodienamine.

    abstract::The Pictet-Spengler reaction of tryptamine type 1,2-dihydropyridine 5c derived from the cycloaddition of the sec-nitrodienamine 3c with acetaldehyde afforded the indoloquinolizine derivatives 6 and 7. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1898

    authors: Koike T,Shinohara Y,Tobinaga S,Takeuchi N

    更新日期:2000-12-01 00:00:00

  • Preparation of 4-pentenoic acid ester of Neu5Ac and 4-pentenyl glycoside of Neu5Ac and their application to glycosylation.

    abstract::Novel sialosyl donors, 4-pentenoic acid ester of N-acetylneuraminic acids (Neu5Ac) and 4-pentenyl glycoside of Neu5Ac were successfully prepared from the corresponding per-O-acetylated 2-hydroxy and 2-chloro derivatives of Neu5Ac, respectively and applied to the synthesis of O-sialosides. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1490

    authors: Ikeda K,Fukuyo J,Sato K,Sato M

    更新日期:2005-11-01 00:00:00

  • Preparation of 9-hydroxy grayanotoxin derivatives and their acute toxicity in mice.

    abstract::Novel 9alpha and 9beta-hydroxy grayanotoxin II derivatives were prepared by photo-sensitized oxygenation of iso-grayanotoxin II and oxidation of grayanotoxin II tetraacetate with selenium dioxide respectively. The lethal dosage of 9alpha and 9beta-hydroxy grayanotoxin II were lower than that of grayanotoxin II. In add...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.351

    authors: Terai T,Osakabe K,Katai M,Sakaguchi K,Narama I,Matsuura T,Katakawa J,Tetsumi T

    更新日期:2003-03-01 00:00:00

  • Absolute Structures of Wedelolide Derivatives and Structure-Activity Relationships of Protein Tyrosine Phosphatase 1B Inhibitory ent-Kaurene Diterpenes from Aerial Parts of Wedelia spp. Collected in Indonesia and Japan.

    abstract::Two sesquiterpene lactones with the (9R)-eudesman-9,12-olide framework, wedelolides I and J, have been isolated together with five eudesmanolide sesquiterpenes and twelve ent-kaurene diterpenes from the aerial parts of Indonesian Wedelia prostrata. The absolute configurations of wedelolides I and J, proposed in the pr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00117

    authors: Abdjul DB,Yamazaki H,Kanno SI,Kirikoshi R,Tomizawa A,Takahashi O,Maarisit W,Losung F,Rotinsulu H,Wewengkang DS,Sumilat DA,Kapojos MM,Namikoshi M

    更新日期:2018-01-01 00:00:00

  • A hepatitis B virus inhibitory neolignan from Herpetospermum caudigerum.

    abstract::A new dihydrobenzofuran neolignan, herpepropenal, was isolated from the seeds of Herpetospermum caudigerum. Its chemical structure was established based on spectroscopic analysis. In this work, the inhibitory effects of herpepropenal on hepatitis B virus DNA and on the replication and expression of hepatitis B surface...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.402

    authors: Yang F,Zhang HJ,Zhang YY,Chen WS,Yuan HL,Lin HW

    更新日期:2010-03-01 00:00:00

  • Crystal structure of the alcoholates and the ansolvate of PNU-97018, an angiotensin II receptor antagonist.

    abstract::The title compound, PNU-97018 [systemic name: 2-butyl-3,6,7,8,9,11-hexahydro-6,9-dimethyl-3-([2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl)-6,9-ethano-4H-imidazo[4,5-d]-pyridazino[1,2-a]pyridazin-4-one] is a newly developed angiotensin II receptor antagonist. The compound and its methanolate and ethanolate were ch...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.1022

    authors: Ishii H,Yamaguchi K,Seki H,Sakamoto S,Tozuka Y,Oguchi T,Yamamoto K

    更新日期:2002-08-01 00:00:00

  • Antifungal activity of fumaric acid in mice infected with Candida albicans.

    abstract::An examination was made on the effect of fumaric acid on an experimental systemic candidiasis. Male ICR mice were innoculated into the tail veins with 10(6) yeast cells of Candida albicans and treated with daily intraperitoneal injections of fumaric acid at the dose of 40 mg/kg/d. The results indicated that the admini...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.3077

    authors: Akao M,Kuroda K

    更新日期:1991-11-01 00:00:00

  • Studies on the constituents of Ailanthus integrifolia.

    abstract::A new phenolic glycoside, 3,4,5-trimethoxyphenol-1-(6-xylopyranosyl)glucopyranoside, was isolated together with twenty known compounds identified as koaburaside, 3,4,5-trimethoxyphenol, 5,7-dihydroxychromone-7-neohesperidoside, naringin, neoeriocitrin, p-coumaric acid, vanillin, vanillic acid, coniferyl aldehyde, feru...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1669

    authors: Kosuge K,Mitsunaga K,Koike K,Ohmoto T

    更新日期:1994-08-01 00:00:00

  • Proton nuclear magnetic resonance study on the aromatic amino acid-guanine nucleotide system: effect of base methylation on the stacking interaction with tyrosine and phenylalanine.

    abstract::The stacking interactions of tyrosine methylester (TyrOMe)-guanosine-5'-monophosphate (GMP), TyrOMe-7-methylguanosine-5'-monophosphate (m7GMP), phenylalanine methylester (PheOMe)-GMP and PheOMe-m7GMP pairs in neutral buffer solution have been studied by proton nuclear magnetic resonance (1H-NMR). The H8 proton signal ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1

    authors: Ishida T,Ohnishi K,Doi M,Inoue M

    更新日期:1989-01-01 00:00:00

  • Three new limonoids from Cipadessa cinerascens.

    abstract::Three new limonoids, cipadesins D--F (1--3), together with 8,15-dihydroxy-13E-labdane, beta-sitosterol and beta-daucosterol, were isolated from the leaves and bark of Cipadessa cinerascens. Their structures were elucidated by spectral evidence. X-Ray crystallographic analysis confirmed the structure of 1. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.902

    authors: Yuan XH,Li BG,Xu CX,Zhou M,Qi HY,Zhang GL

    更新日期:2007-06-01 00:00:00

  • Stilbenoids isolated from stem bark of Shorea hemsleyana.

    abstract::Two new stilbene glucosides [(+)-alpha-viniferin 13b-O-beta-glucopyranoside and resveratrol 12-C-beta-glucopyranoside] and two new resveratrol oligomers, hemsleyanols A and B, were isolated from the bark of Shorea hemsleyana along with four known resveratrol oligomers. The structures of the isolates, including the rel...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1001

    authors: Ito T,Tanaka T,Ido Y,Nakaya KI,Iinuma M,Riswan S

    更新日期:2000-07-01 00:00:00

  • Toxicity of dioxins: role of an absolute hardness-absolute electronegativity diagram (eta-chi diagram) as a new measure in risk assessment.

    abstract::The differences in biological activities among polychlorinated dibenzo-p-dioxins (dioxins) are strongly dependent on the substitution pattern of chlorine at various positions on the parent dibenzo-p-dioxin molecule. The absolute hardness, eta, of dioxins shows a good correlation with the potency of biological activity...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.1780

    authors: Kobayashi S,Sameshima K,Ishii Y,Tanaka A

    更新日期:1995-10-01 00:00:00

  • Antitumor activity of Pulsatilla koreana saponins and their structure-activity relationship.

    abstract::Seventeen saponins isolated from the root of Pulsatilla koreana were examined for their in vitro cytotoxic activity against the human solid cancer cell lines, A-549, SK-OV-3, SK-MEL-2, and HCT15, using the SRB assay method, and their in vivo antitumor activity using BDF1 mice bearing Lewis lung carcinoma (LLC). The sa...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1451

    authors: Bang SC,Lee JH,Song GY,Kim DH,Yoon MY,Ahn BZ

    更新日期:2005-11-01 00:00:00

  • Taxiphyllin 6'-O-gallate, actinidioionoside 6'-O-gallate and myricetrin 2″-O-sulfate from the leaves of Syzygium samarangense and their biological activities.

    abstract::Three new compounds were isolated from a MeOH extract of the leaves of Syzygium samarangense, one new cyanogenic glucoside, taxiphyllin 6'-O-gallate (1), one new megastigmane glucoside, actinidioionoside 6'-O-gallate (2), and one new sulfated flavonoid rhamnoside, myricetrin 2″-O-sulfate (3), together with 14 known co...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c14-00352

    authors: Samy MN,Sugimoto S,Matsunami K,Otsuka H,Kamel MS

    更新日期:2014-01-01 00:00:00

  • Gene delivery into brain capillary endothelial cells using Antp-modified DNA-loaded nanoparticles.

    abstract::Our aim is to test the characteristics and expression activity in brain capillary endothelial cells (BCECs) of DNA-loaded nanoparticles before and after the modification with Antennapedia peptide (Antp). Chitosan (CH), polyethylenimine (PEI) and polyamidoamine (PAMAM) were chosen to prepare the nanoparticles; Lipofect...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1254

    authors: Huang R,Yang W,Jiang C,Pei Y

    更新日期:2006-09-01 00:00:00

  • Design, Synthesis, and Biological Evaluation of Beauveriolide Analogues Bearing Photoreactive Amino Acids.

    abstract::Beauveriolides I and III, which are naturally occurring cyclodepsipeptides, have been reported to bind to sterol O-acyltransferase (SOAT), inhibiting its ability to synthesize cholesteryl esters. To facilitate an analysis of the binding site(s) of these compounds, we designed beauveriolide analogues 1a-d wherein the L...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00095

    authors: Masuda Y,Aoyama K,Yoshida M,Kobayashi K,Ohshiro T,Tomoda H,Doi T

    更新日期:2016-07-01 00:00:00

  • Synthesis and triplex-forming ability of 2',4'-BNAs bearing imidazoles as a nucleobase.

    abstract::To expand the sequence of double-stranded DNA (dsDNA) targets in a triplex formation, 2',4'-BNAs (2'-O,4'-C-methylene bridged nucleic acids) having imidazoles as a nucleobase were synthesized and incorporated into oligonucleotides. Triplex-forming ability of the modified oligonucleotides was evaluated by using melting...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.843

    authors: Hari Y,Obika S,Inohara H,Ikejiri M,Une D,Imanishi T

    更新日期:2005-07-01 00:00:00

  • A convenient synthesis of immunosuppressive agent FTY720 using the petasis reaction.

    abstract::A convenient synthesis of immunosuppressive agent FTY720 (1) using the Petasis reaction was developed. 4-Octylbenzaldehyde (9) was converted into 1-ethenyl-4-octylbenzene (11) by two-step synthesis. Hydroboration of 11 using catecholborane and hydrolysis gave (E)-2-(4-octylphenyl)vinylboronic acid (4). The Petasis rea...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.100

    authors: Sugiyama S,Arai S,Kiriyama M,Ishii K

    更新日期:2005-01-01 00:00:00

  • New 5-HT3 (serotonin-3) receptor antagonists. IV. Synthesis and structure-activity relationships of azabicycloalkaneacetamide derivatives.

    abstract::The synthesis and structure-activity relationships of a series of new azabicycloalkanes as 5-HT3 (serotonin-3) receptor antagonists are described. Our study on the azabicycloalkaneacetamide derivatives showed that 2,3-dihydroindole as the aromatic ring moiety afforded potent 5-HT3 receptor antagonist activity, as judg...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.1351

    authors: Kato M,Ito K,Nishino S,Yamakuni H,Takasugi H

    更新日期:1995-08-01 00:00:00

  • Properties of gastroretentive sustained release tablets prepared by combination of melt/sublimation actions of L-menthol and penetration of molten polymers into tablets.

    abstract::A novel floating sustained release tablet having a cavity in the center was developed by utilizing the physicochemical properties of L-menthol and the penetration of molten hydrophobic polymer into tablets. A dry-coated tablet containing famotidine as a model drug in outer layer was prepared with a L-menthol core by d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1221

    authors: Fukuda M,Goto A

    更新日期:2011-01-01 00:00:00

  • Improvement of Pharmaceutical Properties of Zerumbone, a Multifunctional Compound, Using Cyclodextrin Derivatives.

    abstract::Zerumbone is a multifunctional compound which shows various biological activities, such as antitumor activity, anti-inflammatory activity, antiulcer activity, etc. However, to use Zerumbone as functional foods or medicines, its pharmaceutical properties such as solubility should be improved. In the present study, we p...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00621

    authors: Hassan MM,Mohammed AFA,Elamin KM,Devkota HP,Ohno Y,Motoyama K,Higashi T,Imai T

    更新日期:2020-01-01 00:00:00

  • Synthesis of the metabolites of clentiazem.

    abstract::The metabolites of clentiazem in the urine or bile of rats and dogs were investigated. Fifteen basic, 6 acidic, 2 neutral and 4 conjugated metabolites were isolated. In the present paper, fourteen reference compounds as shown in Charts 1, 2 and 3 were synthesized to identify the structures of the metabolites in proced...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.167

    authors: Inoue H,Nakamura S,Otsuka H,Gaino M,Harada T,Matsuki K,Takeda M

    更新日期:1994-01-01 00:00:00

  • Synthesis and pharmacological activity of 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-1-ethyl-2-hydroxymethyl-4- pyrrolidinyl]benzamide (TKS159) and its optical isomers.

    abstract::Of 4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide, four optical isomers, (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, were prepared from optically active 4-amino-1-ethyl-2-hydroxymethylpyrrolidine di-p-toluenesulfonate [(2S,4S)-14, (2S,4R)-17, (2R,4S)-20 and (2R,4R)-23, r...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.1650

    authors: Yanagi T,Kitajima A,Anzai K,Kodama K,Mizoguchi J,Fujiwara H,Sakiyama H,Kamoda O,Kamei C

    更新日期:1999-11-01 00:00:00

  • Evaluation of mitochondrial function by measuring the heat production in state 3 and state 4 respiration.

    abstract::Using a microcalorimetric method, we have measured the heat production in states 3 and 4 respiration of a mitochondrial preparation from rat heart ventricle. Adenosine triphosphate production in state 3 respiration was also determined for the same preparation after heat production was measured. In Tris-buffered soluti...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.3033

    authors: Tamura K,Hayatsu H,Watanabe I,Nakano T,Sugawara Y,Nishii Y

    更新日期:1989-11-01 00:00:00

  • Enzymatic generation of alloxan radicals in rat liver microsomes: possible participation of reduced nicotinamide adenine dinucleotide phosphate (NADPH)-cytochrome P-450 reductase.

    abstract::Electron spin resonance studies showed that addition of rat liver microsomes to the reaction system of alloxan with reduced nicotinamide adenine dinucleotide phosphate (NADPH) resulted in a marked increase in the generation of alloxan radicals (AH.), whereas heat-denatured microsomes were without such effect. Oxidatio...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.432

    authors: Sakurai K,Haga K,Ogiso T

    更新日期:1992-02-01 00:00:00

  • Immunohistochemical demonstration of calcium-binding protein regucalcin in the tissues of rats: the protein localizes in liver and brain.

    abstract::A calcium-binding protein, regucalcin, was isolated from rat liver cytosol. Rabbit-anti-regucalcin antiserum, which was raised against regucalcin conjugated by glutaraldehyde to bovine serum albumin, was applied to glutaraldehyde-fixed whole mounts and subsequently visualized using the peroxidase-antiperoxidase method...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.1601

    authors: Yamaguchi M,Isogai M,Kato S,Mori S

    更新日期:1991-06-01 00:00:00