Synthesis of 12-Methyl-1,2,3,4,6,7,12,12b-octahydro-2,6-methanoindolo[2,3-a]quinokizine
スポンサーリンク
概要
- 論文の詳細を見る
12-Methyl-1,2,3,4,6,7,12,12b-octahydro-2,6-methanoindolo [2,3-a] quinolizine (I), which represents the fundamental skeleton of sarpagine type indole alkaloids, was synthesized. Thus methyl ester (XI) hydrochloride of N-benzyl-1-methyltryptophan was treated with methy 3-formylpropionate to form tetrahydro-β-carboline derivative (XV), from which 6,10-imino-5H-cyclooct [b] indole dervative (XVII) was prepared by Dieckmann cyclization with sodium hydride under a certain working condition. This was condensed with methyl bromoacetate followed by ketone fission to yield ketoester (XX), from which N-benzyl group was reductively removed and then converted to N-methyl derivative (XXIII).The ethylene thioketal (XXV) of the latter was desulfurized as usual and the product was reduced by lithium aluminum hydride to furnish the corresponding alcohol (XXVII), which was tosylated with tosyl chloride in pyridine in the cold. Spontaneous quaternization of the tosylate took place forming the cyclized quaternary base (XXVIII), the chloride salt of which was submitted to pyrolysis reaction to produced the desired base (I).
- 1965-10-25
著者
-
米田 直人
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
-
米田 直人
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
-
米田 直人
Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
関連論文
- Syntheses and Antimicrobial Activities of α-Isocyanoacrylic Acid Derivatives
- Reaction of Phthalic Anhydrides with Methyl Isocyanoacetate : A Useful Synthesis of 1,2-Dihydro-1-oxoisoquinolines
- A Synthesis of 3-Amino-4-hydroxyquinolin-2 (1H)-one Derivatives via Oxazolo [4,5-c] quinolin-4 (5H)-ones
- Synthesis and Pharmacological Activity of gem-Dialkyl-9-azabicyclo [3,3,1] nonane Derivatives : New Anti-Cholinergic Agent
- 有機燐化合物に対する解毒薬の研究(II) : PAMの合成, PAM類似化合物のスクリーニング及びPAMの定量
- 有機燐化合物に対する解毒薬の研究(I) : 2-Pyridine Aldoxime Methiodide(PAM)の薬理作用
- Studies on Angiotensin Converting Enzyme Inhibitors. III. 2-Carboxyethylcarbamoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Derivatives
- Stereochemistry of Methyl 2-Benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido [3,4-b] indole-1-propionate
- Studies on Angiotensin Converting Enzyme Inhibitors. II. Syntheses and Angiotensin Converting Enzyme Inhibitory Activities of Carboxyethylcarbamoyl-1,2,3,4-tetrahydrosioquinoline-3-carboxylic Acid Derivatives
- Studies on Angiotensin-converting Enzyme Inhibitors. I. Syntheses and Angiotensin-converting Enzyme Inhibitory Activity of 2-(3-Mercaptopropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Derivatives
- Syntheses of α-Alkylated β, γ-Unsaturated α-Amino Acids
- Synthesis of Methyl 2-Isocyano-3-[3 (1H)-indolyl] acrylate and Related Compounds from 3-(Aminomethylene)-3H-indoles
- Convenient Synthesis of 1,4-Thiazane-3-carboxylic Acid Derivatives
- Syntheses of 3-Substituted Pyrrole Derivatives with Antiinflammatory Activity
- Facile Preparation of 5-(3-Indolylmethylene) hydantoins
- Preparation and Reactions of 3-(Aminomethylene)-3H-indoles
- A Convenient Synthesis of α-Substituted Cyclic α-Imino Acids
- Aminomethylation of Thiamine Disulfides and Formation of Cyclobismethylenethiamine from N-Aminomethylated Thiamine Disulfide
- Synthesis of optically Active Prenylamine from (-)-Norephedrine
- The Reaction of S-Aminomethylthiamine with Acid Anhydride : The Synthesis of O, S-Bis (α-aminoacyl) thiamine
- Bis型ビタミンB_1誘導体, Cyclobismethylenethiamineについて : (III)アルカリ分解
- Bis型ビタミンB_1誘導体, Cyclobismethylenethiamineについて : (II)ラネーニッケルによる脱硫反応
- Bis型ビタミンB_1誘導体, Cyclobismethylenethiamineについて : (I)その生成およびο-アシル誘導体の合成
- A New Phosphorylating Reagent. V. The Preparation of α-Glycerophosphoryl Choline and Its Analogues by Means of 2-Chloromethyl-4-nitrophenyl Phosphorodichloridate
- A New Phosphorylating Reagent. IV. The Preparation of the Mixed Phosphoric Diesters of dl-α-Tocopherol and Ethylene Glycol Analogues by Means of 2-Chloromethyl-4-nitrophenyl Phosphorodichloridate
- L-α-Tosylamido-β-propiolactoneの反応(第3報) : メルカプタン類との反応
- Thiamine Disulfide Monobenzoateにかんする研究 : (I)Thiamine Disulfide Monobenzoateの合成
- Reactions of L-α-Tosylamino-β-propiolactone. II. A Novel Synthesis of L-Seryl Peptides
- 7.Bis型ビタミンB_1誘導体, Dipyrimidocyclooctanoate化合物について(II)DPCDの分解反応(日本ビタミン学会 第21回大会研究発表要旨)
- 6.Bis型ビタミンB_1誘導体, Dipyrimidocyclooctadecane化合物について(I)DPCDの生成およびO-アシル誘導体の合成(日本ビタミン学会 第21回大会研究発表要旨)
- L-α-Tosylamido-β-propiolactoneの反応(第1報) : L-α-Tosylamido-β-propiolactoneの合成およびアミン類との反応ならびにL-Serineへの誘導
- Synthesis of 12-Methyl-1,2,3,4,6,7,12,12b-octahydro-2,6-methanoindolo[2,3-a]quinokizine
- Synthesis of 12-Methyl-1,2,3,4,6,7,12,12b-octahydro-2,6-methanoindolo[2,3-a]quinolizine
- Synthesis of 9,10-Dimethoxy-1,2,3,4,6,7-hexahydro-2,6-methano-11bH-benzo [a] quinolizine