Total synthesis of (+/-)-gleenol and (+/-)-axenol via a functionalized spiro[4.5]decane.

Abstract:

:Total synthesis of the biologically important axane sesquiterpenes, gleenol (1) and axenol (2), was accomplished through a readily available spiro[4.5]decane. The key features of the synthesis of 1 and 2 include Claisen rearrangement to afford the multi-functionalized spiro[4.5]decane 4 as a single diastereomer in excellent yield, installation of the C7 isopropyl group via ketene dithioacetal instead of direct alkylation and a diastereoselective reduction of ketone under the Birch conditions.

authors

Nakazaki A,Era T,Kobayashi S

doi

10.1248/cpb.55.1606

subject

Has Abstract

pub_date

2007-11-01 00:00:00

pages

1606-9

issue

11

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/55.1606

journal_volume

55

pub_type

杂志文章
  • Separation of sympathomimetic amines of abuse and related compounds by micellar electrokinetic chromatography.

    abstract::Separation of twelve sympathomimetic amines and related compounds by micellar electrokinetic chromatography (MEKC) with UV absorbance detection is described. These amines were well separated within 25 min using 50 mM sodium tetraborate solution containing 15 mM sodium dodecylsulfate (SDS) of pH 9.3 as a running soluti...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.905

    authors: Kuroda N,Sato D,Ohyama K,Wada M,Nakahara Y,Nakashima K

    更新日期:2001-07-01 00:00:00

  • Benzylidene 2-aminoimidazolones derivatives: synthesis and in vitro evaluation of anti-tumor carcinoma activity.

    abstract::A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human ca...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00340

    authors: Ling Y,Wang ZQ,Xiao YA,Zhu C,Shen L,Wang XM,Hui Y,Wang XY

    更新日期:2013-01-01 00:00:00

  • Technetium-99m complexes with steroid-2-aminooxyethyliminodiacetic acid conjugates.

    abstract::Conjugates of 2-aminooxyethyliminodiacetic acid with estrone, testosterone, epiandrosterone, 17-alpha-hydroxy-progesterone and progesterone were synthesized and their complexes with Tc-99m were successfully prepared in good yields, which indicated the agent to be promising for metal-labeling of biomolecules and relate...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.413

    authors: Yoda R,Karube Y,Takata J,Nagata Y,Matsushima Y

    更新日期:1999-03-01 00:00:00

  • The effects of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose on rat liver mitochondrial respiration.

    abstract::The inhibitory effects of pure galloylglucose (1,2,3,4,6-penta-O-galloyl-beta-D-glucose) on the respiratory chain of rat liver mitochondria were investigated. The respiratory control ratio (RCR) decreased by 50% on addition of 20 microM pentagalloylglucose to highly coupled mitochondria, but the adenosine-5'-diphospha...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1341

    authors: Adachi H,Konishi K,Horikoshi I

    更新日期:1989-05-01 00:00:00

  • Characterization of sodium hypochlorite degradation of beta-glucan in relation to its metabolism in vivo.

    abstract::Soluble (SSG, beta-1,3-D-glucan obtained from the culture filtrates of a fungus, Sclerotinia sclerotiorum IFO 9395) and particulate (zymosan) beta-glucans were oxidized by sodium hypochlorite (NaClO), and the oxidized products were analyzed by gel filtration and ion-exchange chromatographies and by limulus G-test to s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.2137

    authors: Miura NN,Ohno N,Adachi Y,Yadomae T

    更新日期:1996-11-01 00:00:00

  • CCR5 antagonists as anti-HIV-1 agents. 1. Synthesis and biological evaluation of 5-oxopyrrolidine-3-carboxamide derivatives.

    abstract::A novel lead compound, N-(3-[4-(4-fluorobenzoyl)piperidin-1-yl]propyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide (1), was identified as a CCR5 antagonist by high-throughput screening using [(125)I]RANTES and CCR5-expressing CHO cells. The IC(50) value of 1 was 1.9 microM. In an effort to improve the binding aff...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.63

    authors: Imamura S,Ishihara Y,Hattori T,Kurasawa O,Matsushita Y,Sugihara Y,Kanzaki N,Iizawa Y,Baba M,Hashiguchi S

    更新日期:2004-01-01 00:00:00

  • New diarylheptanoids from Amomum muricarpum ELMER.

    abstract::Two new diarylheptanoids, designated muricarpones A and B, together with three known diarylheptanoids, 1,7-di-(3',4'-dihydroxyphenyl)-4-hepten-3-one, 1-(3',4'-dihydroxyphenyl)-7-(4''-hydroxyphenyl)-4-hepten-3-one, and 1,7-bis(p-hydroxyphenyl)-4-hepten-3-one, were isolated from the rhizomes of Amomum muricarpum ELMER (...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.139

    authors: Giang PM,Son PT,Matsunami K,Otsuka H

    更新日期:2006-01-01 00:00:00

  • A chemical approach to searching for bioactive ingredients in cigarette smoke.

    abstract::Cigarette smoke, a collection of many toxic chemicals, contributes to the pathogenesis of smoking-related diseases such as chronic obstructive pulmonary disease and cancer. Much work has been done on the chemical analysis of ingredients in cigarette smoke, but there are few reports on the active ingredients that can m...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00539

    authors: Takahashi Y,Horiyama S,Honda C,Suwa K,Nakamura K,Kunitomo M,Shimma S,Toyoda M,Sato H,Shizuma M,Takayama M

    更新日期:2013-01-01 00:00:00

  • Preparation of optically active threo-2-amino-3-hydroxy-3-phenylpropanoic acid (threo-beta-phenylserine) via optical resolution.

    abstract::To obtain optically active threo-2-amino-3-hydroxy-3-phenylpropanoic acid (1), (2RS,3SR)-2-benzoylamino-3-hydroxy-3-phenylpropanoic acid [(2RS,3SR)-2] was first optically resolved using (1S,2S)- and (1R,2R)-2-amino-1-(4-nitrophenyl)-1,3-propanediol as the resolving agents to afford (2R,3S)- and (2S,3R)-2 in yields of ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.1363

    authors: Shiraiwa T,Saijoh R,Suzuki M,Yoshida K,Nishimura S,Nagasawa H

    更新日期:2003-12-01 00:00:00

  • Synthesis and biological activities of analogs of a lipid A biosynthetic precursor: 1-O-phosphonooxyethyl-4'-O-phosphono-disaccharides with (R)-3-hydroxytetradecanoyl or tetradecanoyl groups at positions 2, 3, 2' and 3'.

    abstract::Two novel analogs of a biosynthetic precursor of lipid A (2) were synthesized. The one analog (3) has acyl groups identical to those of 2, and the other (4) has tetradecanoyl groups in place of the (R)-3-hydroxytetradecanoyl groups of 2. Both 3 and 4 possess an alpha-glycosidically-bound phosphonooxyethyl group in pla...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.1994

    authors: Kusama T,Soga T,Ono Y,Kumazawa E,Shioya E,Osada Y,Kusumoto S,Shiba T

    更新日期:1991-08-01 00:00:00

  • Synthesis and structure-activity relationships of new (5R,8R,10R)-ergoline derivatives with antihypertensive or dopaminergic activity.

    abstract::A series of new (5R,8R,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were tested in conscious spontaneously hypertensive rats and in rats with unilateral 6-hydroxydopamine-induced lesions of the substantia nigra. (5R,8R,10R)-6-Alkyl-8-ergolinemethanols, prepared from...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1463

    authors: Ohno S,Adachi Y,Koumori M,Mizukoshi K,Nagasaka M,Ichihara K,Kato E

    更新日期:1994-07-01 00:00:00

  • Studies on the synthesis of compounds related to adenosine 3',5'-cyclic phosphate. VII. Synthesis and cardiac effects of N6,N6-dialkyl adenosine 3',5'-cyclic phosphates.

    abstract::A series of novel N6,N6-dialkyl adenosine 3',5'-cyclic phosphates N6,N6-dialkyl cAMPs) was synthesized from 2'-O-p-toluenesulfonyl cAMP (2'-O-tosyl cAMP, 2) and tested for inotropic and chronotropic activities in vitro. Treatment of 2 with excess alkyl halides and sodium hydride followed by detosylation with aqueous N...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.3147

    authors: Kataoka S,Yamaji N,Kato M,Kawada T,Imai S

    更新日期:1990-11-01 00:00:00

  • Studies on the 1,4-oxazepine ring formation reaction using the molecular orbital method.

    abstract::1,4-Oxazepine formation reactions of 1,8-naphthyridine derivatives (1-4) with peroxy acid have been studied using a semiempirical MO method (AM1) and an ab initio molecular orbital method (Gaussian 94). The energies of molecules involved in the reaction paths were calculated and the transition states related to experi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.755

    authors: Matsuzaki H,Takeuchi I,Hamada Y,Hatano K

    更新日期:2000-05-01 00:00:00

  • Novel hypotensive peptides from the body of Elaphe climacophora.

    abstract::Four hypotensive peptides called elapherine-A, -B, -C and -D were isolated from the body of Elaphe climacophora after removal of the internal organs. Elapherine-A, which had the lowest molecular weight, exhibited a prolonged fall for 5 min in the blood pressure of spontaneously hypertensive rats, whereas elapherin-B, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.1004

    authors: Tsujibo H,Sato H,Taniguchi T,Kamatani Y,Kenny PT,Nomoto K,Inamori Y

    更新日期:1990-04-01 00:00:00

  • Statistical Analysis of the Impact of Molecular Descriptors on Cytotoxicity of Thiourea Derivatives Incorporating 2-Aminothiazole Scaffold.

    abstract::Chemical reactivity descriptors and lipophilicyty (log P) were evaluated via semi-empirical method for the quantum calculation of molecular electronic structure (PM3) in order to clarify the structure-cytotoxic activity relationships of disubstutited thioureas. Analysed compounds were obtained by the linkage of 2-amin...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00317

    authors: Filipowska A,Filipowski W,Tkacz E,Nowicka G,Struga M

    更新日期:2016-01-01 00:00:00

  • Preparations of anthraquinone and naphthoquinone derivatives and their cytotoxic effects.

    abstract::Chrysophanol and 1,8-di-O-hexylchrysophanol derivatives having nucleic acid bases at position 5 were synthesized. Furthermore, derivatives of menadione substituted at position 11 (type A naphthoquinone derivatives) or methylmenadione substituted at position 7 (type B naphthoquinone derivatives) modified with nucleic a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.302

    authors: Cui XR,Saito R,Kubo T,Kon D,Hirano Y,Saito S

    更新日期:2011-01-01 00:00:00

  • Russuphelin A, a new cytotoxic substance from the mushroom Russula subnigricans Hongo.

    abstract::A new cytotoxic substance, designated russuphelin A (1), has been isolated from the mushroom Russula subnigricans Hongo (Basidiomycetes). The structure was elucidated as 2,6-bis(2,6-dichloro-4-hydroxyphenyloxy)-1,4-dimethoxy-benzene on the basis of spectroscopic data and confirmed by total synthesis. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.3185

    authors: Takahashi A,Agatsuma T,Matsuda M,Ohta T,Nunozawa T,Endo T,Nozoe S

    更新日期:1992-12-01 00:00:00

  • Microbial metabolites of harman alkaloids.

    abstract::Several microorganisms showed the ability to transform the harman alkaloids, harmaline (1), harmalol (2) and harman (5). Harmaline (1) and harmalol (2) were converted by Rhodotorula rubra ATCC 20129 into the tryptamines, 2-acetyl-3-(2-acetamidoethyl)-7-methoxyindole (3) and 2-acetyl-3-(2-acetamidoethyl)-7-hydroxyindol...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.646

    authors: Herath W,Mikell JR,Ferreira D,Khan IA

    更新日期:2003-06-01 00:00:00

  • Change of ras-transformed NRK-cells back to normal morphology by mycalamides A and B, antitumor agents from a marine sponge.

    abstract::Mycalamide A and mycalamide B, isolated as antiviral and antitumor agents from a New Zealand sponge of the genus Mycale, converted the morphology of ras-transformed NRK-cells to normal morphology at 10 and 1 ng/ml, respectively. The effect on protein synthesis suggests that these agents converted the morphology by pre...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.2152

    authors: Ogawara H,Higashi K,Uchino K,Perry NB

    更新日期:1991-08-01 00:00:00

  • Two new phenolic amides from the seeds of Pharbitis nil.

    abstract::Two new phenolic amides, pharnilatins A (1) and B (2), were isolated from the seeds of Pharbitis nil. These new compounds possess a p-coumaroyl unit with a structurally unique side chain, (2S,3S)-2,3-dihydroxyputrescine. The chemical structures and absolute stereochemistries of the new compounds were determined on the...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1532

    authors: Kim KH,Choi SU,Son MW,Lee KR

    更新日期:2010-11-01 00:00:00

  • Method for optical resolution of racemic homochlorcyclizine and comparison of optical isomers in antihistamine activity and pharmacokinetics.

    abstract::A method was developed for semi-preparative scale enantioseparation of racemic homochlorcyclizine (HCZ) by high performance liquid chromatography (HPLC) on Chiralcel OD column. The best resolution was achieved using an eluent composed of n-hexane plus 0.2 M isopropylamine. By this method, about 5.0 mg of racemic HCZ c...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1341

    authors: Nishikata M,Nakai A,Fushida H,Miyake K,Arita T,Kitagawa S,Kunitomo M,Iseki K,Miyazaki K

    更新日期:1992-05-01 00:00:00

  • Hepatic calcium-binding protein regucalcin decreases Ca2+/calmodulin-dependent protein kinase activity in rat liver cytosol.

    abstract::The effect of regucalcin, a calcium-binding protein isolated from rat liver cytosol, on cytosolic Ca2+/calmodulin-dependent protein kinase activity was investigated. The increase in cytosolic Ca2+/calmodulin-dependent protein kinase activity with passage of incubation time was clearly prevented by the presence of regu...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2216

    authors: Mori S,Yamaguchi M

    更新日期:1990-08-01 00:00:00

  • Tyrokeradines C-F, new bromotyrosine alkaloids from the Verongid sponges.

    abstract::Four new bromotyrosine alkaloids, tyrokeradines C-F (1-4), have been isolated from Okinawan marine sponges of the order Verongidae. The structures of 1-4 were elucidated on the basis of spectroscopic data. Tyrokeradines C (1) and D (2) are new bromotyrosine alkaloids possesing an imidazole ring, while tyrokeradines E ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00785

    authors: Kubota T,Watase S,Mukai H,Fromont J,Kobayashi J

    更新日期:2012-01-01 00:00:00

  • Characteristics of hyaluronate-hydroxyethyl acrylate blend gel and release of cationic amphiphilic solutes.

    abstract::Hyaluronate-hydroxyethyl acrylate blend gel (HA-PHEA) were prepared to modify the brittleness of hyaluronate gel (HA) and the characteristics of HA-PHEA gel were compared with those of HA and polyhydroxyethyl acrylate (PHEA) gels. These gels were high in water content and transparent. HA-PHEA gel was improved in visco...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.1341

    authors: Jin Y,Yamanaka J,Sato S,Miyata I,Yomota C,Yonese M

    更新日期:2002-10-01 00:00:00

  • Design, synthesis, and cytotoxic activity of Michael acceptors and enol esters in the benzo[b]acronycine series.

    abstract::A series of 2-acyl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (4-6) was prepared by treatment of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (3) with an excess of an appropriate acyl chloride in the presence of aluminum chloride. Treatment of (+/-)-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.919

    authors: Doan Thi Mai H,Gaslonde T,Michel S,Koch M,Tillequin F,Bailly C,David-Cordonnier MH,Pfeiffer B,Léonce S,Pierré A

    更新日期:2005-08-01 00:00:00

  • Total Synthesis and Anticancer Activity of Novel Pulsatilla Saponin D Analogues.

    abstract::Novel saponins that retain a free carboxyl group at the C-17 position and various sugars linked at the C-3 position of hederagenin aglycone were synthesized via stereospecific glycosylation. Since these natural products represented by Pulsatilla saponin D (PSD) were obtained in very small amounts, the total synthesis ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00106

    authors: Kim M,Park Y,Chung WY,Park KK,Jung M

    更新日期:2015-01-01 00:00:00

  • Prolonged Distribution of Tranilast in the Eyes after Topical Application onto Eyelid Skin.

    abstract::Tranilast, a lipophilic drug with various ophthalmic applications, was used as a model drug to establish the possibility of delivering lipophilic drugs through the eyelid skin. Pharmacokinetics and tissue distribution studies were conducted employing three application methods (topical application onto eyelid skin, eye...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00289

    authors: See GL,Arce F Jr,Itakura S,Todo H,Sugibayashi K

    更新日期:2020-01-01 00:00:00

  • New sesquiterpenes and calebin derivatives from Curcuma longa.

    abstract::One novel sesquiterpene with new skeleton, (6S)-2-methyl-6-(4-hydroxyphenyl-3-methyl)-2-hepten-4-one (1), two new bisabolane sesquiterpenes, (6S)-2-methyl-6-(4-hydroxyphenyl)-2-hepten-4-one (2), (6S)-2-methyl-6-(4-formylphenyl)-2-hepten-4-one (3), and two calebin derivatives, 4''-(4'''-hydroxyphenyl-3'''-methoxy)-2''-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.940

    authors: Zeng Y,Qiu F,Takahashi K,Liang J,Qu G,Yao X

    更新日期:2007-06-01 00:00:00

  • Stability of Mixed Preparations Consisting of Commercial Moisturizing Creams with an Ointment Base Investigated by Magnetic Resonance Imaging.

    abstract::A moisturizing cream mixed with a steroid ointment is frequently prescribed to patients suffering from atopic dermatitis. However, there is a concern that the mixing operation causes destabilization. The present study was performed to investigate the stability of such preparations closely using magnetic resonance imag...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00986

    authors: Onuki Y,Funatani C,Yamamoto Y,Fukami T,Koide T,Hayashi Y,Takayama K

    更新日期:2017-01-01 00:00:00

  • Protection of a new heptapeptide from Carapax trionycis against carbon tetrachloride-induced acute liver injury in mice.

    abstract::A new heptapeptide GAGPHGG (OC1) was isolated from Carapax trionycis which was a traditional Chinese medicine (TCM) used for treatment of hepatic diseases. The structure of OC1 was characterized by MS, NMR techniques, together with amino acid sequence analysis. The hepatoprotective activity of OC1 was evaluated in viv...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00442

    authors: Wang P,Zhang Y,An Y,Xu K,Xu X,Fu C,Lin J,Xu S,Li Q,Lei H

    更新日期:2013-01-01 00:00:00