Efficient Synthesis of (22R, 23R, 24S)-22, 23-Isopropylidenedioxy-5α-ergost-2-en-6-one, a Key Intermediate in the Preparation of Brassinolide(Organic Chemistry)
スポンサーリンク
概要
- 論文の詳細を見る
(22R, 23R, 24S)-22, 23-Isopropylidenedioxy-5α-ergost-2-en-6-one 2b is an important intermediate of brassinolide. We found that the enone 2b can be prepared by transformation of (22R, 23R, 24S)-3α, 5-cyclo-22, 23-isopropylidenedioxy-5α-ergostan-6-one 5b with catalytic amount of both p-TsOH and NaBr in DMF under reflux. 5b was prepared from (22R, 23R, 24S)-3α, 5-cyclo-22, 23-dihydroxy-6β-methoxy-5α-ergostane 9b or a 6β-benzyloxy compound 9c, which was obtained in a manner similar to Mori's brassinolide synthesis. The enone 2b was eventually prepared via a benzyl ether 9c from stigmasterol 3a in a 15.5% yield in 11 steps.
- 社団法人日本農芸化学会の論文
- 1986-12-23
著者
-
Aburatani M
Research Division Fuji Chemical Industries Ltd.
-
TAKEUCHI Tadashi
Research Division, Fuji Chemical Industries Ltd.
-
Aburatani Masakazu
Research Division Fuji Chemical Industries Ltd.
-
Takeuchi Tadashi
Institute Of Microbial Chemistry
-
Mori Kenji
Department Of Biochemistry National Cardiovascular Center Research Institute
-
Takeuchi Tadashi
Research Division Fuji Chemical Industries Ltd.
-
Mori Kenji
Department Of Agricultural Chemistry Nagoya University
-
Mori Kenji
Department Of Agricultural Chemistry College Of Science And Technology The University Of Tokyo
関連論文
- C-type Natriuretic Peptide, a Novel Antifibrotic Agent, Attenuates Cardiac Remodeling and Improves Left Ventricular Dysfunction in Dilated Cardiomyopathy(Cardiovascular Pharmacology, Basic/Clinical 1 (H), The 69th Annual Scientific Meeting of the Japanese
- Calcineurin-NFAT Pathway-Dependent Cardiac Remodeling in Mice Deficient for GC-A, a Receptor for Atrial and Brain Natriuretic Peptides(Cardiac Hypertrophy 1 (M), The 69th Annual Scientific Meeting of the Japanese Circulation Society)
- Interaction between C-Type Natriuretic Peptide and Endothelin-1 in Hypertrophic Response of Cultured Rat Cardiac Myocytes
- Endogenous Endothelin-1 Secreted from Cultured Rat Cardiac Nonmyocytes Inhibits Doxorubicin-Induced Cardiac Myocyte Apoptosis via ERK-Dependent CREB Activation
- A case of Kabuki syndrome presenting West syndrome
- Effect of Introducing a Lactone Group into Typhasterol and Teasterone to Promote Rice Lamina Inclination
- Stereoselective Synthesis of Methyl Epijasmonate(Organic Chemistry)
- Trial of intraventricular ribavirin therapy for subacute sclerosing panencephalitis in Japan
- Neuronal protein NP25 interacts with F-actin
- Neuronal protein25は神経細胞の分化により増加する
- Pathophysiology of the transient temporal lobe lesion in a patient with Menkes disease
- Serial brain imaging analysis of stroke-like episodes in MELAS
- Favorable response of ADHD with giant SEP to extended-release valproate
- Administration of secretin for autism alters dopamine metabolism in the central nervous system
- Synthesis of 4-Hydroxy-3(2H)-furanone Acyl Derivatives and Their Anti-cataract Effect on Spontaneous Cataract Rats (ICR/f)
- Antioxidative Activities of 4-Hydroxy-3 (2H)-furanones and Their Anti-cataract Effect on Spontaneous Cataract Rat (ICR/f)
- Synthesis of Methyl (5Z, 9Z, 17R)-17-Methylnonadeca-5, 9-dienoate, the (R)-Enantiomer of the Structure Proposed for a Metabolite of the Philippine Sponge Plakinastrella sp.(Organic Chemistry)
- Patients with West syndrome whose ictal SPECT showed focal cortical hyperperfusion
- A case of acute encephalitis with refractory, repetitive partial seizures, presenting autoantibody to glutamate receptor Gluε2
- Successful Management of Intractable Epilepsy with Lidocaine Tapes and Continuous Subcutaneous Lidocaine Infusion
- A case of idiopathic portal hypertension associated with rheumatoid arthritis
- Synthesis of Both the Enantiomers of trans-Chrysanthenol and trans-Chrysanthenyl Acetate as the Characteristic Major Constituents of Kougiku
- Synthesis of All Four Possible Stereoisomers of 1-Phenyl-2,3-butanediol and Both Enantiomers of 3-Hydroxy-4-phenyl-2-butanone to Determine the Absolute Configuration of the Natural Constituents
- Simple Synthesis of Dehydrololiolide
- Synthesis of (±)-Methyl Epijasmonate and (±)-Methyl Cucurbate(Organic Chemistry)
- A Simple and Efficient Synthesis of (±)-Methyl Dihydroepijasmonate(Organic Chemistry)
- Stereoselective Synthesis of erythro-Serricornin, (4R, 6R, 7S)-, and (4596R, 75)-4?6-Dimethyl-7-hydroxynonan-3-one9 Stereoisomers of the Sex Pheromone of Cigarette Beetle
- Molecular Action Mode of Hippospongic Acid A, an Inhibitor of Gastrulation of Starfish Embryos
- Biological activity of pestalotins on the elongation growth of rice seedlings
- Subtilisin-Like Proprotein Convertases, PACE4 and PC8, as Well as Furin, are Endogenous Proalbumin Convertases in HepG2 Cells
- Biological Activities of YTIT/YTIY Analogous Sequences Present in Fibronectin-Like Type III Repeats
- A remarkable large hamartoma around the knee in a patient with tuberous sclerosis
- Long-term follow-up of a patient with subacute sclerosing panencephalitis successfully treated with intrathecal interferon alpha
- Adrenocorticotropic hormone therapy for infantile spasms alters pyruvate metabolism in the central nervous system
- Behavioral and Electroantennogram Responses of Male American Cockroaches to Periplanones and Their Analogs(Organic Chemistry)
- Pb7 HAUPTMANN'S PERIPLANONE-A : CHARACTERIZATION AND ELUCIDATION OF THE FORMATION
- Syntheses of Four Methyl-branched Secondary Acetates and a Methyl-branched Ketone as Possible Candidates for the Female Pheromone of the Screwworm Fly, Cochliomyia hominivorax(Organic Chemistry)
- Syntheses of Racemic and Diastereomeric Mixtures of 3,7,11,15-Tetramethylhentriacontane and 4,8,12,16-Tetramethyldotriacontane, the Cuticular Tetramethylalkanes of the Tsetse Fly, Glossina brevipalpis(Organic Chemistry)
- Concise Synthesis of a Racemic and Diastereomeric Mixture of the Sex Pheromones of Matsucoccus Pine Scales
- Determination of the (2E, 4E)-Geometry of the 3,5-Dimethyl-2,4-diene System of Antibiotic 1233A by NMR Comparison with the Four Geometrical Isomers of Methyl 3,5-Dimethyl-2,4-heptadienoate
- Percutaneous hot water injection and microwave coagulation therapy for small hepatocellular carcinoma
- New Anthracycline Antibiotics 10-epi-Oxaunomycin and 10-epi-11-Deoxyoxaunomycin
- Genomic Organization and Alternative Splicing of Human PACE4 (SPC4), Kexin-Like Processing Endoprotease
- Synthesis of (+)-Turmeronol A, an Inhibitor of Soybean Lipoxygenase, and (+)-ar-Turmerone
- Human Subtilisin-Like Proprotein Convertase, PACE4 (SPC4) Gene Expression Is Highly Regulated through E-Box Elements in HepG2 and GH4C1 Cells
- Synthesis of the Enantiomers of 7-Methyl-1,6-dioxaspiro[4.5]decane, Pheromone of the Common Wasp and the Pine Beetle
- Synthesis of (4aR, 10aS)-(-)-8-Methoxy-1, 1, 4a-trimethyl-2-oxo-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthrene, an Optically Active Intermediate for the Synthesis of Diterpenes(Organic Chemistry)
- Synthesis of (±)-Hiburipyranone, a Cytotoxic Metabolite of Marine Sponge Mycale adhaerens
- Synthesis of the Esterified Cerebroside in the Epidermis of Guinea Pigs
- Reinvestigation of the Structure of the Esterified Cerebroside in the Epidermis of Guinea pigs
- Synthesis of (-)-Allosamizoline, the Pseudoaminosugar Moiety of Allosamidin, a Chitinase Inhibitor
- Brassinolide and Homobrassinolide Promotion of Lamina Inclination of Rice Seedlings
- Synthesis of (R)-Callosobruchusic Acid from Methyl (R)-3-Carboxybutanoate
- Compounds with Juvenile Hormone Activity. I. Inhibitory Effects of the Synthetic Juvenile Hormone and Its Analogues on the Metamorphosis of Several Insects
- New Optically Active 4,4-Dialky1-γ-lactones as Chiral Dopants for Ferroelectric Liquid Crystals
- Synthesis of (S,E)-1-Methyl-9-dodecenyl Acetate, the Sex Pheromone of the Hessian Fly, Mayetiola destructor
- B-10-5 Synthesis of Substances related to Gibberellins(Terpenoids)
- Sex Pheromone of the Comstock Mealybug, Pseudococcus comstocki KUWANA : Isolation and Identification
- Synthesis of Brassinolide Analogs with a Modified Ring B and Their Plant Growth-promoting Activity(Organic Chemistry)
- Juvenile Hormone Activity of Terpeniod Esters and Phenyl-Geranyl-Ethers with Different Alkyl Substituents against the Silkworm, Bombyx mori L. (Lepidoptera : Bombycidae)
- Juvenile Hormone and synthetic Analogues : II. : Novel Substances with High Juvenile Hormone Activity
- Increased Accumulation of Silk Protein Accompanying JH-Induced Prolongation of Larval Life in Bombyx mori L.(Lepidoptera : Bombycidae)
- New Synthesis of Serricornin, the Female Sex Pheromone of the Cigarette Beetle
- Stereoselective Synthesis of Lurlenic Acid and Lurlenol, the Sex Pheromones of the Green Flagellate Chlamydomonas
- Synthesis of (2S,4R,5S)-2,4,6-Trimethyl-5-heptanolide, a Sex Pheromone Component for Macrocentrus grandii
- Synthesis of a Stereoisomeric Mixture of 13,25-, 11,21- and 11,23-Dimethylhepta-triacontane, the Contact Sex Pheromone of the Tsetse Fly, Glossina tachinoides
- Synthesis of 1'-Epi-stegobinone(Organic Chemistry)
- A New Synthesis of Hepialone [(R)-2-Ethyl-6-methyl-2,3-dihydro-4H-pyran-4-one], the Principal Component from Male Sex Scales of the Ghost Moth, Hepialus californicus B
- Indium-Catalyzed Cross-Coupling Reactions between α, β-Unsaturated Carbonyl Compounds and Aromatic Aldehydes
- InCl_3-Catalyzed Reductive Coupling of Aromatic Carbonyl Compounds in the Presence of Magnesium and Chlorotrimethylsilane
- New Synthesis of Macrolide Pheromones of the Flat Grain Beetle, Cryptolestes pusillus Schonherr(Organic Chemistry)
- Synthesis of Gibbilimbols A-D, Cytotoxic and Antibacterial Alkenylphenols Isolated from Piper gibbilimbum
- Inactivation of Proprotein Convertase, PACE4, by α1-Antitrypsin Portland (α1-PDX), a Blocker of Proteolytic Activation of Bone Morphogenetic Protein during Embryogenesis: Evidence That PACE4 Is Able to Form an SDS-Stable Acyl Intermediate with α1- PDX
- A Novel Human PACE4 Isoform, PACE4E Is an Active Processing Protease Containing a Hydrophobic Cluster at the Carboxy Terminus^1
- Effect of Novel Analogs of the Juvenile Hormone. : I. Effect of Juvenile Hormone Analogs with Different Alkyl Substituents at C-7 and C-11 on the Silkworm, Bombyx mori L. (Lepidoptera : Bombycidae)
- New Inorganic-Organic Hybrid Li^+ Ion Conducting Polymer Electrolytes
- A New Synthesis of (-)-exo- Brevicomin
- Efficient Synthesis of (22R, 23R, 24S)-22, 23-Isopropylidenedioxy-5α-ergost-2-en-6-one, a Key Intermediate in the Preparation of Brassinolide(Organic Chemistry)
- Both (4aS,7S,7aR)-(+)-Nepetalactone and Its Antipode Are Powerful Attractants for Cats (Organic Chemistry)
- Synthesis of (1R,2S)-1-(3'-Chloro-4'-methoxyphenyl)-1,2-propanediol (Trametol) and (1R,2S)-1-(3',5'-Dichloro-4'-methoxyphenyl)-1,2-propanediol, Chlorinated Fungal Metabolites in the Natural Environment(Organic Chemistry)
- Biological Activities of the Analogs of the Aggregation Pheromone of Tribolium castaneum(Coleoptera : Tenebrionidae)
- Synthesis of Both the Enantiomers of (6Z,9Z)-cis-3,4-Epoxy-6,9-heptadecadiene, the Pheromone Component of Various Geometrid Moths
- Purification of a Peptide from Rat Brain
- PB93 A NEW STEREOSELECTIVE SYNTHESIS OF (-)-PERIPLANONE-B
- Synthesis of the Four Stereoisomers of 3,12-Dimethylheptacosane, (Z)-9-Pentacosene and (Z)-9-Heptacosene, the Cuticular Hydrocarbons of the Ant, Diacamma sp.(Organic Chemistry)
- Synthesis of 2-(4-Hydroxyphenyl) naphthalene-1,8-dicarboxylic Anhydride, a Phytoalexin Isolated from Unripe Banana (Musa acuminata)
- Synthesis of (R)-(+)-Hippospongic Acid A, a Triterpene Isolated from the Marine Sponge, Hippospongia sp.(Organic Chemistry)
- Synthesis of the Enantiomers of Some Methyl-branched Cuticular Hydrocarbons of the Ant, Diacamma sp.
- Synthesis of 2,2,4,4-Tetramethyl-N, N'-bis (2,6-dimethylphenyl) cyclobutane-1,3-diimine, a Unique Compound from Arundo donax, and Its Analogues to Test Their Antifeedant Activity Against the Boll Weevil, Anthonomus grandis
- New Syntheses of the Rice Moth and Stink Bug Pheromones by Employing (2R, 6S)-7-Acetoxy-2,6-dimethyl-1-heptanol as a Building Block
- Synthesis of (+)-Juvabione, a Compoud with Juvenile Hormone Activity
- Simple Synthesis of a Diastereomeric Mixture of 2-(3', 4'-Epoxy-4'-methylcyclohexyl)-6-methyl-2,5-heptadiene, the Pheromone of the Green Stink Bug
- Synthesis of Both the Enantiomers of Aseanostatin P5(Sarcinic Acid), an Inhibitor of Myeloperoxidase Release, and Four Diastereomers of Aggreceride A, a Platelet Aggregation Inhibitor
- Synthesis of (-)-Biopterin Using (S)-Ethyl Lactate as a Starting Material(Organic Chemistry)
- Synthesis of (1R,3S,5S)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid Moth Endoclita excrescens, and Its Enantiomer
- Synthesis of the Enantiomers of 2,6-Dimethyl-6-hepten-1-ol, a Mandibular Gland Secretion of the Male Ant Lasius niger(Organic Chemistry)
- Synthesis of (2S,2'R,3R,4E,8E)-N-2'-Hydroxyoctadecanoyl-1-O-(β-D-glucopyranosyl)-9-methyl-4,8-sphingadienine (Pen III), a Cerebroside Isolated from Penicillium funiculosum as the Fruiting Inducer against Schizophyllum commune
- A Simple Preparation of (-)-Khusimone (1) Using Electrochemical Decarboxylative Acetylation(Organic Chemistry)
- Synthesis of Both the Enantiomers of (Z)-cis-9,10-Epoxy-6-heneicosene(Organic Chemistry)
- Facile Syntheses of Brassinosteroids: Brassinolide, Castasterone, Teasterone and Typhasterol