天然含窒素複素環の化学(その1)数種の植物に出現するBenzo[α]quinolizidine環系及びIndolo[2,3-α]quinolizidine環系アルカロイドの合成と構造決定
スポンサーリンク
概要
- 論文の詳細を見る
Nineteen benzo[α]quinolizidine alkaloids (1-19) isolated so far from Alangium plants can be classified into four types (I-IV) according to their chemical structures. Studies on racemic and chiral syntheses of these I-IV-type alkaloids are reviewed with particular emphasis on the strategies and tactics for the syntheses employed by the author. It has been found that racemic syntheses of all of these types of alkaloids are possible through the "lactim ether route" or the "3-acetylpyridine route"; and chiral syntheses, through the "cincholoipon-incorporating route" or the "chiral lactim ether route". As a result of such total syntheses, the structures and absolute configurations of four II-type, two III- type, and two IV-type Alangium alkaloids have been established. Extensions of the "chiral lactim ether route" to the syntheses of the Ochrosia alkaloid (-)-ochropposinine [ (-)-93g], the Neisosperma alkaloid (-)-ochromianine [(-)-97], and the Ophiorrhiza alkaloid (-)-ophiorrhizine [(-)-98] have unequivocally established the absolute stereochemistries of these three indolo[2,3-α]-quinolizidine alkaloids.
- 社団法人日本薬学会の論文
- 1996-05-25
著者
関連論文
- 天然含窒素複素環の化学(その2)プリン塩基・ヌクレオシドの合成と反応
- 天然含窒素複素環の化学(その1)数種の植物に出現するBenzo[α]quinolizidine環系及びIndolo[2,3-α]quinolizidine環系アルカロイドの合成と構造決定
- 含窒素複素環の化学 : 私の40年
- 日本薬学会教育賞受賞笹本光雄氏の業績
- 日本薬学会学術賞紹介 日野亨氏の業績
- Purines. LXX. An Extension of the "Phenacylamine Route" to the Syntheses of the 7-N-Oxides of 6-Mercaptopurine and 6-Methylthiopurine, and Antileukemic Activity of Some Purine N-Oxides
- Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
- Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
- Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
- Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
- Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
- Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
- Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
- Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines
- Variable glyceryl dinitrate formation as a function of glutathione S-transferase.
- Variable Glyceryl Dinitrate Formation as a Function of Glutathione S-Transferase
- Quinolizidines. XXVI. : A Synthesis of (±)-Deplancheine
- Purines. XLI. : An Alternative Synthesis and the Chemical Behavior of 7,9-Dialkyladeninium Salts
- Purines. XXXVIII. A General Synthesis of 7,9-Dialkyladeninium Salts from 9-Alkyladenines by Regioselective Alkylation : Utilization of an N^6-Alkoxy Group as a Control Synthon
- Purines. XXX. : Ring Fission of 3,7-Dialkyladenines by Alkaline Hydrolysis
- Purines. XXVIII. Preparation of Some 3,7-Dialkyladenines from 3-Alkyladenines by Alkylation : A Subordinate Formation of 3,9-Dialkyladenines
- Preparation of New Nitrogen-Bridged Heterocycles. 58. : Syntheses and Intramolecular Arene-π Interactions of 3-(Allylthio)- and 3-(Propargylthio)thieno[3,4-b]indolizine Derivatives
- Preparation of New Nitrogen-Bridged Heterocycles. 54. Increased Arene-Arene Interactions of 3-(Bicyclic and Tricyclic Arylmethylthio)thieno[3,4-b]indolizine Derivatives
- Preparation of New Nitrogen-Bridged Heterocycles. 53. Syntheses of 3-(Benzylthio)thieno[3,4-b]indolizine Derivatives and Their Intramolecular Arene-Arene Interactions
- ゼアチンおよび N^6- イソペンテニルアデニンの 1'- メチル誘導体とそれらのリボヌクレオシド体のレタス種子発芽におけるサイトカイニン活性について(A. 理学)
- Purines. LXII. Both Enantiomers of N^6-(1,3-Dimetyl-2-butenyl)adenine and Their 9-β-D-Ribofuranosides : Synthesis and Cytokinin Activity
- Purines. LV. Syntheses and cytokinin activities of some adenine and adenosine derivatives related to 1'-methylzeatin
- Pourines. XLV. : Syntheses and Cytokinin Activities of the Cis Isomers of (1'R)-1'-Methylzeatin and Its 9-β-D-Ribofuranoside
- Purines. XXXV. : Synthesis and Cytokinin Activity of Racemic 1'-Methylzeatin
- Purines. XXXIII. Syntheses and Cytokinin Activities of Both Enantiomers of 1'-Methylzeatin and Their 9-β-D-Ribofuranosides
- P-3 海綿由来アデニン環含有ジテルペノイドの合成研究 : (±)-Agelasimine-Aおよび(±)-Agelasimine-Bの合成(ポスター発表の部)
- Purines. LXV. Preparatory study for the syntheses of the marine sponge purines agelasimines-A and -B: Synthesis and acetylation of their N(7)-benzyl analogues
- Purines. LXIV. Syntheses of 9-Methyl-2-azaadenine 1-Oxide, Its O-Methyl Derivative, and 1-Substituted 5-Azidoimidazole-4-carboxamides
- Purines. LXIII. Syntheses of Azepinomycin, an Antitumor Antibiotic from Streptomyces Species, and Its 3-β-D-Ribofuranodise and Their 8-Imino Analogues
- Purines. LXI. An Attempted Synthesis of 2'-Deoxy-7-methyladenosine : Glycosidic Hydrolyses of the N^6-Methoxy Derivative and 2'-Deoxy N^x-methyladenosines
- Purines. LIX. An Alternative Synthesis of 7-Alkyl-1-methyladenines by Regioselective Alkylation, Fission, and Reclosure of the Adenine Ring
- Purines. LVIII. A Synthesis of 7-Alkyl-1-methyladenines from Adenosine by Regioselective Alkylation : Uilization of a 1-Methoxy Group as a Control Synthon
- Purines. LVII. Regioselective Alkylation of N^6,9-Disubstituted 8-Oxoadenines : Syntheses of the Sea Anemone Purine Caissarone and Some Positional Isomers and Analogues
- Purines. LIV. Intramolecular Cyclization of 9-Ethyl-1-(2-hydroxyethyl)adenine Caused by Nucleophiles : Formation of N^6,1-Ethanoadenine Derivatives
- Purines. LIII. Deamination of 1-(ω-Hydroxyalkyl)adenine Derivatives by Nucleophiles
- Purines. XLIX. Synthesis and Proton Nuclear Magnetic Resonance Study of 3,7-Dialkylxanthines and 1,3,7-Trialkylxanthines
- Purines. XLVIII. Syntheses and Proton Nuclear Magnetic Resonance Study of 2-Deuterioadenines Substituted or Unsubstituted at the 9-Position and of Their N-Oxygenated Derivatives
- Purines. XLVI. Preparation of 1-Ethyladenine from Adenosine
- Quinolizidines. XX. Racetnic and Chiral Syntheses of the Alangium Alkaloids 9-Demethylprotoemetinol and 10-Demethylprotoemetinol(Organic,Chemical)
- Quinolizidines. XXV. : An Extension of the "Lactim Ether Route" to the Racemic Syntheses of Several Indolo[2,3-α]quinolizidine Alkaloids
- Quinolizidines. XVIII. Synthesis of (-)- and (+)-ankorines through a lactim ether route
- Synthesis of 5-(Alkylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamides : Key Intermediates for the Synthesis of 3-Alkyl-9-β-D-ribofuranosylpurine Derivatives
- Purines. XXXII. : Synthesis and Ring Fission of 3,9-Dialkyladenines
- Purines. XXIX. Syntheses of 9-Alkyl-2-deuterio-N^6-methoxyadenines and 2-Deuterio-N^6,9-dimethyladenine : Tautomerism in 9-Substituted N^6-Alkoxyadenines(Organic,Chemical)
- Benzoquinolizidine環系ウリノキ科アルカロイドの構造と合成
- Quinolizidines. XXXIII. A chiral synthesis of (-)-ophiorrhizine, a pentacyclic quaternary indole alkaloid from ophiorrhiza major RIDL
- Syntheses of several cyclopentano-monoterpene lactones using 1,3-dioxin vinylogous ester
- Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines
- 植物塩基の解体と組換え : Alangiumアルカロイドの合成と構造研究の戦略
- Purines. LXXIX. Synthesis and Hydrolysis of 3-Methoxyadenine and Its N^6-Benzyl Derivative Leading to the Corresponding 2-Hydroxyadenines
- Purines. LXXVIII. An Alternative Synthesis of the Sea Anemone Purine Alkaloid Caissarone
- Purines. IXXVII. An Alternative Synthesis of N^6-Demethylcaissarone from 9-Methyl-8-oxoadenine by Regioselective N(3)-Methylation : Utilization of the N(7)-Benzyl and N(1)-Benzyloxy Groups as Control Synthons
- Purines. LXXVI. Alkylation of 8-Oxoadenine Derivatives : Syntheses of 3,7-Dialkyl-, 3,9-Dialkyl-, and 3,7,9-Trialkyl-8-oxoadenines
- Purines. LXXV. Dimroth Rearrangement, Hydrolytic Deamination, and Pyrimidine-Ring Breakdown of 7-Alkylated 1-Alkoxyadenines : N(1)-C(2) versus N(1)-C(6) Bond Fission
- Purines. LXXIV. Syntheses and Rearrangements of 8-Oxoadenines Monomethylated at the N^6-, 1-, and 3-Positions
- Purines. LXXII. Oxidation of N^6-Alkyladenines with m-Chloroperoxybenzoic Acid Leading to N^6-Alkyladenine 1-Oxides
- Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines
- The alkaline phosphatase in human plexus chorioideus.
- Purines. XLVII. Dimroth Rearrangement versus Hydrolytic Deamination of 1-Ethyladenine
- Quinolizidines. XXX. A ready access to the dibenzo[a,f]quinolizidine ring system from 1,2,3,4-tetrahydroquinoline
- Syntheses of cis-Zeatin and Its 9-(2-Deoxy-β-D-ribofuranosyl) Derivative : A Novel Synthetic Route to the Side Chain at C(6), and Cytokinin Activity
- Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana
- Quinolizidines. XXVII. Racemic and chiral syntheses of the Neisosperma and Ochrosia alkaloid ochropposinine
- Quinolizidines. XXIV. : Syntheses of Ankorine Congeners in Different Oxidation States
- Quinolizidines. XIX. Synthesis of (-)-9-demethyltubulosine
- Purines. XXXVII. : Synthesis and Reduction of 3,9-Diallkyladenine Salts Deuterated at the 2-Position : Their Use in the Proton Nuclear Magnetic Resonance Study of Isotopically Unmodified Species
- Purines.XXXIX. : The Crystal Structure of 9-Benzyl-N^6-methoxyadenine
- Purines. XXXI. : An X-Ray Crystallographic Structure Analysis of 3-Methyladenosine p-Toluenesulfonate
- Purines. XLIV. : A Kinetic Study of the Dimroth Rearrangement of the Marine Sponge Purine 1,9-Dimethyl-8-oxoadenine and Related Compounds
- Purines. XLIII. : A Total Synthesis of the Marine Sponge Base 6-Imino-1,9-dimethyl-8-oxopurine
- 53 桿菌tRNA構成成分,7-Methyladenosineの合成と加水分解(口頭発表の部)
- Purines. XLII. : Synthesis and Glycosidic Hydrolysis of 7-Alkyladenosines Leading to an Alternative Synthesis of 7-Alkyladenines
- Purines. XL. : Preparation of 9-(ω-Carboxyalkyl)-3-methyladenines
- Purines. XXXVI. : Fission and Reclosure of the Adenine Ring in 3,9-Disubstituted Adenines : Effects of Substituents
- Purines. XXXIV. : 3-Methyladenosine and 3-Methyl-2'-deoxyadenosine : Their Synthesis, Glycosidic Hydrolysis, and Ring Fission
- A General and Convenient Synthesis of 7-Alkyladenines from Adenine by Regioselective Alkylation Utilizing Blocking/Deblocking at the 3-Position
- Purines. XXVII. : Hydrolytic Deamination versus Dimroth Rearrangement in the 9-Substituted Adenine Ring : Effect of an ω-Hydroxyalkyl Group at the 1-Position
- ラクタム類の研究(第16報)X線結晶解析による1-Benzyl-5-ethyl-1,2,5,6-tetrahydro-2-oxo-4-pyridineacetic Acidの分子構造
- アデニン環の開裂と再閉環