Special Issue

Adolf Butenandt's Special Issues, Vol. 10, No. 1, 1978

49 data found. 31 - 49 listedFirst Previous
Communication | Special issue | Vol 10, No. 1, 1978, pp. 199 - 205
Published online:
DOI: 10.3987/S-1978-01-0199
Synthesis and Reactivity of Heterocyclic α-Diazo Carbonyl Compounds

Axel Schmitz, Udo Kraatz, and Friedhelm Korte*

*Institut für Organische Chemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany

Abstract

Synthesis of α-diazo substituted 3-carboxylic esters of isoxazolone and pyrazolone (3a,b) by diazo group transfer succeeds only with the use of the azidinium salt 2.
The thermodynamically quite stable diazo compounds 3a, b are very resistant to mineral acids but can be readily coupled to form azo derivatives with compounds containing an active C-H bond. Hydrolysis of their labile phosphazines 6a, and b readily gives the hydrazones 7a,b.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 207 - 220
Published online:
DOI: 10.3987/S-1978-01-0207
Synthesis of A-Thienosteroids and Related Compounds

Taichiro Komeno,* Hikozo Iwakura, and Ken’ichi Takeda

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan

Abstract

The Grignard reaction of optically active 1,5-dioxo-7α-methyl-3aα,7aβ-hexahydroindan-4α-yl acetic acid with 2- and 3-thienyl magnesium bromide, followed by lactonization gave thienyl γ-lactones, 8a and 8b, respectively. Their configurations were established by the dipole moments. They were converted through multi-steps to a number of A-thienosteroids, namely modified steroids in which the ring A are displaced by fused thiophenes. A-thiolenone derivatives also were prepared from these A-thienosteroids.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 221 - 228
Published online:
DOI: 10.3987/S-1978-01-0221
Nucleophilic Reactions of 5,6-Dihydronicotinic Acid Esters and a Novel Method for the Preparation of 1,4,5,6-Tetrahydropyridine-3-carboxylic Acid Esters

Ulrich Renner*

*Pharmaceuticals Division, Research Department, Ciba-Geigy Limited, CH-4002 Basel, Switzerland

Abstract

Reaction of 1,5-diaminopentan-3-one V with ethyl acetoacetate yielded diazaspiro-undecadiene-dicarboxylic acid ester VI by a one-step synthesis. Novel 4-aroyl- 1,4,5,6-tetrahydropyridine-3-carboxylic acid esters XI and condensed analogs XI11 have been prepared by cycloaddition of ethyl acetoacetate to α-methylene-6-aminopropiophenones or their cyclized analogs respectively.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 229 - 235
Published online:
DOI: 10.3987/S-1978-01-0229
Structure Dependent Reactivity in the Oxygenation of Thiane Analogs by a Cytochrome P-450 Recon-stituted Enzyme System

Tadashi Takahashi, Y. H. Kim, Daikichi Fukushima, Ken Fujimori, Shigeru Oae,* and Takashi Iyanagi

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan

Abstract

Thiane analogs were oxidized to the corresponding sulfoxides by the reconstituted system of purified rabbit liver microsomal cytochrome P-450 — NADPH-cytochrome P-450 reductase. The stereochemical results and kinetic behaviors were discussed in comparison with those of the nonenzymatic oxidations of the thiane analogs by NaIO4. The enzymatic oxygenation of thianes was found to be nonstereospecific, however, the rates of the enzymatic oxygenation was found to be effected by the hydrophobicity of the substrate.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 237 - 240
Published online:
DOI: 10.3987/S-1978-01-0237
Synthesis of B-Homoaporphine Skeleton. Steric Requirements in the Formation of the Phenanthro[10,1-b,c]azepine System

Ichiya Ninomiya* and Takeaki Naito

*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan

Abstract

B-Homoaporphine skeletons (4a and b) were prepared via two routes; the photocyclization of the 1-phenyloxazolo[4,3-a][2]benzazepin-3-one (1) and the Friedel-Crafts-type cyclization of 2-oxophenanthro[9,10-d]oxazoline-3-propionic acid (6c).

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 241 - 245
Published online:
DOI: 10.3987/S-1978-01-0241
Synthesis of Imidazo[4,5-b]pyridines

Isao Hayakawa,* Ken-ichi Yamazaki, Renzo Dohmori, and Naofumi Koga

*Exploratory Research Laboratories I, Daiichi Pharmaceutical Co., Ltd., 16-13, Kitakasai 1-chome, Edsogawa-ku, Tokyo 134, Japan

Abstract

Novel syntheses of an imidazo[4,5-b]pyridine and its alkyl derivatives were studied and the structures of the products were determined.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 247 - 250
Published online:
DOI: 10.3987/S-1978-01-0247
Synthesis of Tritium and of Deuterium Labelled Pteridines of High Activity

Heinz Rembold* and Günter Hennings

*Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Gottingen, Germany

Abstract

2,4-Diamino-6,7-dimethylpteridine and 2-amino-4-hydroxy-6,7-dimethylpteridine were synthetized with high specific 3H and 2D labelling in the 6,7- and the 7-methyl groups. The isotopes are stable in these positions. No HT- or HD-exchange could be observed.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 251 - 256
Published online:
DOI: 10.3987/S-1978-01-0251
The Primary Structure of the Monomeric Hemoglobin (Erythrocruorin)Component CTT-of Chironomus thummi thummi (Insecta, Diptera)

Traute Kleinschmidt, Helgan yon der Mark-Neuwirth and Gerhard Braunitzer*

*Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Gottingen, Germany

Abstract

The amino acid sequence of the monomeric component CTT-I, one of 12 of the hemoglobins (Erythrocruorins) of larvae of Chironomus thummi thummi (Insecta, Diptera) is given. The sequence and the side chains forming the heme complex are discussed.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 257 - 260
Published online:
DOI: 10.3987/S-1978-01-0257
Annelation by Intramolecular 1,3-Dipolar Addition of Nitrones

Takenori Kusumi, Satoru Takahashi, Yoko Sato, and Hiroshi Kakisawa*

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan

Abstract

Intramolecular 1,3-dipolar cyclization of the nitrone 2 gave the perhydroindane 5 as a regio and stereoselective product.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 261 - 264
Published online:
DOI: 10.3987/S-1978-01-0261
Reaction of β-Aminocrotonamides with α-Haloketones and α-Hydroxyketones

Tetsuzo Kato,* Takuo Chiba, Masaki Noda, and Makoto Sasaki

*Pharmaceutical Institute, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

Reaction of bromoacetophenone (4) with β-aminocrotonamide (1) and β-aminocrotonanilide (2) gave 2-methyl-5-phenylpyrrole-3-carboxamide (6) and 2-methyl-5-phenylpyrrole-3-carboxanilide (7), respectively. Similarly, 2-chlorocyclohexanone (5) reacted with (1), (2) and β-amino-(N-methyl)crotonamide (3) to give 2-methyl-4,5,6,7-tetrahydroindole-3-carboxamide derivatives (8, 9 and 10).
Reactions of α-hydroxyketones such as benzoin (11) and acetoin (12) with (1), (2) and (3) afforded 2-methylpyrrole-3-carboxamide derivatives (13 - 18).

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 265 - 268
Published online:
DOI: 10.3987/S-1978-01-0265
Synthesis of Multicyclic Keto Lactams by the Photo-ring-expansion of N-(1-Adamantyl)succinimides

Masanao Terashima, Kazue Ohkura, Haruo Okajima and Yuichi Kanaoka*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

Upon irradiation N-(1-adamantyl)succinimides with carbocyclic substituents on the imide ring undergo the ring-expansion reaction in fairly good yields affording various multicyclic keto lactam systems.

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Communication | Special issue | Vol 10, No. 1, 1978, pp. 269 - 276
Published online:
DOI: 10.3987/S-1978-01-0269
Reactivity of Imidazo [1,2-b]pyridazine 1-Oxides

Kazue Satoh and Tadashi Miyasaka*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan

Abstract

The treatment of either imidazo[1,2-b]pyridazines (III) or their 1-oxides (III) with excess organic peracid resulted in the oxidative cleavage of imidazole moiety to give 3-(N-acylhydroxylamino)pyridazines (IV). The bromination and nitration of II gave the corresponding 3-substituted N-oxides (VII, IX, X, and XI). Rearrangement reaction of II with phosphoryl chloride or acetic anhydride afforded the deoxygenated 7-substituted imidazopyridazines, XII and XIII, respectively.

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Review | Special issue | Vol 10, No. 1, 1978, pp. 277 - 347
Published online:
DOI: 10.3987/S-1978-01-0277
Pathophysiologische Bedeutung von L-Carnosin auf die Wundheilung

Kineshiro Nagai* and Toshio Yamane

*School of Dentistry at Niigata, The Nippon Dental University, Hamaura-cho 1-8, Niigata 951, Japan

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Review | Special issue | Vol 10, No. 1, 1978, pp. 349 - 390
Published online:
DOI: 10.3987/S-1978-01-0349
Annelation Reaction by Using Heterocyclic Compounds

Tetsuji Kametani* and Hideo Nemoto

*Pharmaceutical Institute, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

This review deals with the recent advances in the use of heterocvclic compounds as annelating reagents, especially as applied to the synthesis of natural products.

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Review | Special issue | Vol 10, No. 1, 1978, pp. 391 - 412
Published online:
DOI: 10.3987/S-1978-01-0391
Synthesis and Cytokinin-Agonistic and Antagonistic Activities of Substituted Pyrrolo[2,3-d]pyrimidines: Development of Anticytokinins

Hajime Iwamura*

*Kyoto University, Yoshida, Sakyou-ku, Kyoto 606-8501, Japan

Abstract

Recent studies of cytokinin antagonists were reviewed, with special attention on substituted pyrrolo[2,3-d]pyrimidines. Principles for the design of anticytokinin-active compounds, their specific antagonistic nature, agonist-antagonist descrimination and chemical structure/activity relationship in terms of steric bulk of side chain and the utilization of anticytokinins in studies of plant growth are the major objects discussed.

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Review | Special issue | Vol 10, No. 1, 1978, pp. 413 - 423
Published online:
DOI: 10.3987/S-1978-01-0413
Carbon-13 Nuclear Magnetic Resonance Studies of Colletotrichins and Their Biosynthesis

Yasuo Kimura,* Masatoshi Gohbara, Akinori Suzuki, and Saburo Tamura

*Department of Agricultural Chemistry, Faculty of Agricultural and Life Sciences, University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan

Abstract

The 13C-nmr spectra of three related secondary fungal metabolites, colletotrichin (I), colletotrichin B (II), and C (III), isolated from Colletotrichum nicotianae have been studied. Labelling patterns of these compounds derived from 13c-formate, 1-13C-, 2-13C-, and 1,2-13C-acetates, and 5-13C-mevalonate have been determined. These compounds were proved to be biosynthesized in combination of acetate-mevalonate-geranyl-geranyl pyrophosphate route with acetate-polyketide route. Moreover, a new pathway, which involves cyclization of geranyl geranyl pyrophosphate into I, II, and III was proposed.

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Review | Special issue | Vol 10, No. 1, 1978, pp. 425 - 467
Published online:
DOI: 10.3987/S-1978-01-0425
Piericidins: Naturally Occurring Inhibitors against Mitochondrial Respiration

Shigeo Yoshida* and Nobutaka Takahashi

*Department of Agricultural Chemistry, Faculty of Agricultural and Life Sciences, University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan

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Review | Special issue | Vol 10, No. 1, 1978, pp. 469 - 553
Published online:
DOI: 10.3987/S-1978-01-0469
Total Syntheses of Natural Products from Five-membered Heterocyclic Compounds as Starting Materials

Tetsuji Kametani* and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

Total syntheses of natural products, in which the carbon-unit generated by ring opening of five-membered heterocyclic compounds is either a starting material or a key intermediate, are described.

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Review | Special issue | Vol 10, No. 1, 1978, pp. 555 - 595
Published online:
DOI: 10.3987/S-1978-01-0555
Syntheses of 5,10b-Ethanophenanthridine and Related Alkaloids Occurring in Amaryllidaceae

Yoshisuke Tsuda*

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

Synthetic works on the titled compounds including the following articles are reviewed.

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